Substituted 2-heteroaryloxypyridines and salts thereof and their use as herbicidal agents

- Bayer Aktiengesellschaft

Substituted 2-heteroaryloxypyridines and salts thereof and use thereof as herbicidal active substances Substituted 2-heteroaryloxypyridines of the general formula (I) are described, and their use as herbicides, in particular for controlling broad-leaved weeds and/or weed grasses in crops of useful plants and/or as plant growth regulators for influencing the growth of crops of useful plants. The present invention further relates to herbicidal and/or plant growth-regulating compositions comprising one or more compounds of the general formula (I).

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Description
CROSS-REFERENCE TO RELATED APPLICATIONS

This application is the National Stage entry of International Application No. PCT/EP2019/066197, filed 19 Jun. 2019, which claims priority to European Patent Application No. 18179566.7, filed 25 Jun. 2018.

BACKGROUND Field

The invention relates to the technical field of crop protection agents, in particular that of herbicides for the selective control of broad-leaved weeds and weed grasses in crops of useful plants.

Specifically, the present invention relates to substituted 2-heteroaryloxypyridines and salts thereof, to processes for their preparation and to their use as herbicides.

Description of Related Art

In their application, crop protection agents known to date for the selective control of harmful plants in crops of useful plants or active compounds for controlling unwanted vegetation sometimes have disadvantages, be it (a) that they have no or else insufficient herbicidal activity against particular harmful plants, (b) that the spectrum of harmful plants which can be controlled with an active compound is not wide enough, (c) that their selectivity in crops of useful plants is too low and/or (d) that they have a toxicologically unfavorable profile. Furthermore, some active compounds which can be used as plant growth regulators for a number of useful plants cause unwanted reduced harvest yields in other useful plants or are not compatible with the crop plant, or only within a narrow application rate range. Some of the known active compounds cannot be produced economically on an industrial scale owing to precursors and reagents which are difficult to obtain, or they have only insufficient chemical stabilities. In the case of other active compounds, the activity is too highly dependent on environmental conditions, such as weather and soil conditions.

The herbicidal activity of these known compounds, in particular at low application rates, and/or their compatibility with crop plants remain in need of improvement.

WO2011/22313 names 2-heteroaryloxypyridines which are described as components of pharmaceutical utility which act on glutamate receptors. In addition, heteroaryloxybenzenes to which herbicidal action has been attributed have been described in WO2015/89003, WO2015/108779, WO2016/10731, WO2016/196606 and WO2017/11288.

However, substituted 2-heteroaryloxypyridines or salts thereof as herbicidally active compounds have hitherto not been described.

SUMMARY

Surprisingly, it has now been found that substituted 2-heteroaryloxypyridines or salts thereof are particularly suitable as herbicidally active compounds.

Accordingly, the present invention provides substituted 2-heteroaryloxypyridines of the general formula (I) or salts thereof


in which

    • X represents nitrogen, —CF— or —CH—,
    • A represents oxygen, —S(O)n—, —C(R4)(R5)—, —C(═O)— or —NR6—
    • with n=0, 1 ort,
    • R1 represents optionally substituted aryl, heteroaryl, heterocyclyl, (C3-C10)-cycloalkyl or (C3-C10)-cycloalkenyl, where each ring or each ring system is optionally substituted by up to 5 substituents independently selected from the group R7;
    • R2 independently of the others represents halogen, cyano, nitro, formyl, formamide, (C1-C8)-alkyl, (C1-C8)-haloalkyl, (C2-C8)-alkenyl, (C2-C8)-alkynyl, (C2-C8)-haloalkenyl, (C2-C8)-haloalkynyl, (C1-C4)-alkoxy-(C1-C4)-alkyl, (C1-C4)-haloalkoxy-(C1-C4)-alkyl, (C1-C4)-alkylthio-(C1-C4)-alkyl, (C1-C4)-alkylsulfinyl-(C1-C4)-alkyl, (C1-C4)-alkylsulfonyl-(C1-C4)-alkyl, (C1-C8)-alkylcarbonyl, (C1-C8)-haloalkylcarbonyl, (C3-C8)-cycloalkylcarbonyl, carboxyl, (C1-C8)-alkoxycarbonyl, (C1-C8)-haloalkoxycarbonyl, (C3-C8)-cycloalkoxycarbonyl, carbamoyl, (C2-C8)-alkylaminocarbonyl, (C2-C10)-dialkylaminocarbonyl, (C3-C10)-cycloalkylaminocarbonyl, (C1-C4)-alkoxycarbonyl-(C1-C4)-alkyl, (C1-C4)-haloalkoxycarbonyl-(C1-C4)-alkyl, carboxy-(C1-C4)-alkyl, hydroxy, amino, (C1-C8)-alkoxy, (C1-C8)-haloalkoxy, (C1-C8)-alkylthio, (C1-C8)-haloalkylthio, (C3-C8)-cycloalkylthio, (C1-C8)-alkylsulfinyl, (C1-C8)-haloalkylsulfinyl, (C3-C8)-cycloalkylsulfinyl, (C1-C8)-alkylsulfonyl, (C1-C8)-haloalkylsulfonyl, (C3-C8)-cycloalkylsulfonyl, (C1-C8)-alkylaminosulfonyl, (C2-C8)-dialkylaminosulfonyl or (C3-C8)-trialkylsilyl,
    • m represents 0, 1, 2 or 3,
    • R3 represents hydrogen, halogen, cyano, nitro, formyl, (C1-C8)-alkyl, (C1-C8)-haloalkyl, (C2-C8)-alkenyl, (C2-C8)-alkynyl, (C2-C8)-haloalkenyl, (C2-C8)-haloalkynyl, (C1-C4)-alkoxy-(C1-C4)-alkyl, (C1-C4)-haloalkoxy-(C1-C4)-alkyl, (C1-C4)-alkylthio-(C1-C4)-alkyl, (C1-C4)-alkylsulfinyl-(C1-C4)-alkyl, (C1-C4)-alkylsulfonyl-(C1-C4)-alkyl, (C1-C8)-alkylcarbonyl, (C1-C8)-haloalkylcarbonyl, (C3-C8)-cycloalkylcarbonyl, carboxyl, (C1-C8)-alkoxycarbonyl, (C1-C8)-haloalkoxycarbonyl, (C3-C8)-cycloalkoxycarbonyl, (C1-C8)-alkylaminocarbonyl, (C2-C8)-dialkylaminocarbonyl, (C3-C8)-cycloalkylaminocarbonyl, hydroxy, (C1-C8)-alkoxy, (C1-C8)-haloalkoxy, (C1-C8)-alkylthio, (C1-C8)-haloalkylthio, (C3-C8)-cycloalkylthio, (C1-C8)-alkylsulfinyl, (C1-C8)-haloalkylsulfinyl, (C3-C8)-cycloalkylsulfinyl, (C1-C8)-alkylsulfonyl, (C1-C8)-haloalkylsulfonyl, (C3-C8)-cycloalkylsulfonyl, (C1-C8)-alkylaminosulfonyl, (C2-C8)-dialkylaminosulfonyl or (C3-C8)-trialkylsilyl,
    • R4 and R5 independently of one another represent hydrogen, hydroxy, halogen, (C1-C8)-alkyl, (C1-C8)-haloalkyl, (C2-C8)-alkenyl, (C2-C8)-alkynyl, (C1-C4)-alkoxy-(C1-C4)-alkyl, (C1-C4)-haloalkoxy-(C1-C4)-alkyl, (C1-C4)-alkylthio-(C1-C4)-alkyl, (C1-C4)-alkylsulfinyl-(C1-C4)-alkyl, (C1-C4)-alkylsulfonyl-(C1-C4)-alkyl, (C1-C8)-alkylcarbonyl, (C1-C8)-haloalkylcarbonyl, (C3-C8)-cycloalkylcarbonyl, (C1-C8)-alkoxycarbonyl, (C1-C8)-haloalkoxycarbonyl, (C3-C8)-cycloalkoxycarbonyl, (C1-C8)-alkylaminocarbonyl, (C2-C8)-dialkylaminocarbonyl, (C3-C8)-cycloalkylaminocarbonyl, (C1-C8)-alkoxy, (C1-C8)-alkylthio, (C1-C8)-haloalkylthio, (C3-C8)-cycloalkylthio,
    • or
    • R4 and R5 together form a 3- to 6-membered carbocyclic ring or a 3- to 6-membered saturated heterocyclic ring having up to 2 oxygen atoms,
    • or
    • R4 and R5 together form a (C1-C3)-alkylidene radical or (C1-C3)-haloalkylidene radical,
    • R6 represents hydrogen, (C1-C8)-alkyl, (C1-C8)-haloalkyl, aryl-(C1-C6)-alkyl, heteroaryl-(C1-C6)-alkyl, (C3-C6)-cycloalkyl, (C3-C6)-cycloalkyl-(C1-C6)-alkyl, (C3-C6)-halocycloalkyl, (C3-C6)-halocycloalkyl-(C1-C4)-alkyl, (C2-C8)-alkenyl, (C2-C8)-alkynyl, (C1-C4)-alkoxy-(C1-C4)-alkyl, (C1-C4)-haloalkoxy-(C1-C4)-alkyl, (C1-C4)-alkylthio-(C1-C4)-alkyl, (C1-C4)-alkylsulfinyl-(C1-C4)-alkyl, (C1-C4)-alkylsulfonyl-(C1-C4)-alkyl, (C1-C8)-alkylcarbonyl, (C1-C8)-haloalkylcarbonyl, (C3-C8)-cycloalkylcarbonyl, formyl, (C1-C8)-alkoxycarbonyl, (C1-C8)-haloalkoxycarbonyl, (C3-C8)-cycloalkoxycarbonyl, (C1-C8)-alkylaminocarbonyl, (C2-C8)-dialkylaminocarbonyl, (C3-C8)-cycloalkylaminocarbonyl,
    • and
    • R7 represents hydrogen, halogen, cyano, nitro, formyl, (C1-C8)-alkyl, (C1-C8)-haloalkyl, (C2-C8)-alkenyl, (C2-C8)-alkynyl, (C2-C8)-haloalkenyl, (C2-C8)-haloalkynyl, (C1-C4)-alkoxy-(C1-C8)-alkyl, (C1-C4)-haloalkoxy-(C1-C4)-alkyl, (C1-C4)-alkylthio-(C1-C4)-alkyl, (C1-C4)-alkylsulfinyl-(C1-C4)-alkyl, (C1-C4)-alkylsulfonyl-(C1-C4)-alkyl, (C1-C8)-alkylcarbonyl, (C1-C8)-haloalkylcarbonyl, (C3-C8)-cycloalkylcarbonyl, carboxyl, (C1-C8)-alkoxycarbonyl, (C1-C8)-haloalkoxycarbonyl, (C3-C8)-cycloalkoxycarbonyl, (C1-C8)-alkylaminocarbonyl, (C2-C8)-dialkylaminocarbonyl, (C3-C8)-cycloalkylaminocarbonyl, hydroxy, (C1-C8)-alkoxy, (C1-C8)-haloalkoxy, (C1-C8)-alkylthio, (C1-C8)-haloalkylthio, (C3-C8)-cycloalkylthio, (C1-C8)-alkylsulfinyl, (C1-C8)-haloalkylsulfinyl, (C3-C8)-cycloalkylsulfinyl, (C1-C8)-alkylsulfonyl, (C1-C8)-haloalkylsulfonyl, (C3-C8)-cycloalkylsulfonyl, (C1-C8)-alkylaminosulfonyl, (C2-C8)-dialkylaminosulfonyl or (C3-C8)-trialkylsilyl.

DETAILED DESCRIPTION OF A PREFERRED EMBODIMENT

The compounds of the general formula (I) can form salts by addition of a suitable inorganic or organic acid, for example mineral acids, for example HCl, HBr, H2SO4, H3PO4 or HNO3, or organic acids, for example carboxylic acids such as formic acid, acetic acid, propionic acid, oxalic acid, lactic acid or salicylic acid or sulfonic acids, for example p-toluenesulfonic acid, onto a basic group, for example amino, alkylamino, dialkylamino, piperidino, morpholino or pyridino. In such a case, these salts comprise the conjugated base of the acid as the anion. Suitable substituents in deprotonated form, for example sulfonic acids, particular sulfonamides or carboxylic acids, are capable of forming internal salts with groups, such as amino groups, which are themselves protonatable. Salts may also be formed by action of a base on compounds of the general formula (I). Suitable bases are, for example, organic amines such as trialkylamines, morpholine, piperidine and pyridine, and the hydroxides, carbonates and bicarbonates of ammonium, alkali metals or alkaline earth metals, especially sodium hydroxide, potassium hydroxide, sodium carbonate, potassium carbonate, sodium bicarbonate and potassium bicarbonate. These salts are compounds in which the acidic hydrogen is replaced by an agriculturally suitable cation, for example metal salts, especially alkali metal salts or alkaline earth metal salts, in particular sodium and potassium salts, or else ammonium salts, salts with organic amines or quaternary ammonium salts, for example with cations of the formula [NRaRbRcRd]+ in which Ra to Rd are each independently an organic radical, especially alkyl, aryl, arylalkyl or alkylaryl. Also suitable are alkylsulfonium and alkylsulfoxonium salts, such as (C1-C4)-trialkylsulfonium and (C1-C4)-trialkylsulfoxonium salts.

The substituted 2-heteroaryloxypyridines of the general formula (I) according to the invention may, depending on external conditions such as pH, solvent and temperature, be present in various tautomeric structures, all of which are embraced by the general formula (I).

The compounds of the formula (I) used in accordance with the invention and salts thereof are referred to hereinafter as “compounds of the general formula (I)”.

The invention preferably provides compounds of the general formula (I) in which

    • X represents nitrogen, —CF— or —CH—,
    • A represents oxygen, —S(O)n—, —C(R4)(R5)—, —C(═O)— or —NR6—
    • with n=0, 1 or 2,
    • R1 represents optionally substituted aryl, heteroaryl or heterocyclyl, where each ring or each ring system is optionally substituted by up to 5 substituents independently selected from the group R7,
    • R2 independently of the others represents halogen, cyano, nitro, formyl, formamid, (C1-C6)-alkyl, (C1-C6)-haloalkyl, (C2-C6)-alkenyl, (C2-C6)-alkynyl, (C2-C6)-haloalkenyl, (C2-C6)-haloalkynyl, (C1-C4)-alkoxy-(C1-C4)-alkyl, (C1-C4)-haloalkoxy-(C1-C4)-alkyl, (C1-C4)-alkylthio-(C1-C4)-alkyl, (C1-C4)-alkylsulfinyl-(C1-C4)-alkyl, (C1-C4)-alkylsulfonyl-(C1-C4)-alkyl, (C1-C6)-alkylcarbonyl, (C1-C6)-haloalkylcarbonyl, (C3-C6)-cycloalkylcarbonyl, carboxyl, (C1-C6)-alkoxycarbonyl, (C1-C6)-haloalkoxycarbonyl, (C3-C6)-cycloalkoxycarbonyl, carbamoyl, (C2-C6)-alkylaminocarbonyl, (C2-C8)-dialkylaminocarbonyl, (C3-C6)-cycloalkylaminocarbonyl, (C1-C4)-alkoxycarbonyl-(C1-C4)-alkyl, (C1-C4)-haloalkoxycarbonyl-(C1-C4)-alkyl, carboxy-(C1-C6)-alkyl, hydroxy, amino, (C1-C6)-alkoxy, (C1-C6)-haloalkoxy, (C1-C6)-alkylthio, (C1-C6)-haloalkylthio, (C3-C6)-cycloalkylthio, (C1-C6)-alkylsulfinyl, (C1-C6)-haloalkylsulfinyl, (C3-C6)-cycloalkylsulfinyl, (C1-C6)-alkylsulfonyl, (C1-C6)-haloalkylsulfonyl, (C3-C6)-cycloalkylsulfonyl, (C1-C6)-alkylaminosulfonyl, (C2-C8)-dialkylaminosulfonyl or (C3-C8)-trialkylsilyl,
    • m represents 0, 1, 2 or 3,
    • R3 represents hydrogen, halogen, cyano, nitro, formyl, (C1-C6)-alkyl, (C1-C6)-haloalkyl, (C2-C6)-alkenyl, (C2-C6)-alkynyl, (C2-C6)-haloalkenyl, (C2-C6)-haloalkynyl, (C1-C4)-alkoxy-(C1-C4)-alkyl, (C1-C4)-haloalkoxy-(C1-C4)-alkyl, (C1-C4)-alkylthio-(C1-C4)-alkyl, (C1-C4)-alkylsulfinyl-(C1-C4)-alkyl, (C1-C4)-alkylsulfonyl-(C1-C4)-alkyl, (C1-C6)-alkylcarbonyl, (C1-C6)-haloalkylcarbonyl, (C3-C6)-cycloalkylcarbonyl, carboxyl, (C1-C6)-alkoxycarbonyl, (C1-C6)-haloalkoxycarbonyl, (C3-C6)-cycloalkoxycarbonyl, (C1-C6)-alkylaminocarbonyl, (C2-C8)-dialkylaminocarbonyl, (C3-C6)-cycloalkylaminocarbonyl, hydroxy, (C1-C6)-alkoxy, (C1-C6)-haloalkoxy, (C1-C6)-alkylthio, (C1-C6)-haloalkylthio, (C3-C6)-cycloalkylthio, (C1-C6)-alkylsulfinyl, (C1-C6)-haloalkylsulfinyl, (C3-C6)-cycloalkylsulfinyl, (C1-C6)-alkylsulfonyl, (C1-C6)-haloalkylsulfonyl, (C3-C6)-cycloalkylsulfonyl, (C1-C6)-alkylaminosulfonyl, (C2-C8)-dialkylaminosulfonyl or (C3-C8)-trialkylsilyl,
    • R4 and R5 independently of one another represent hydrogen, hydroxy, halogen, (C1-C6)-alkyl, (C1-C6)-haloalkyl, (C2-C6)-alkenyl, (C2-C6)-alkynyl, (C1-C4)-alkoxy-(C1-C4)-alkyl, (C1-C4)-haloalkoxy-(C1-C4)-alkyl, (C1-C4)-alkylthio-(C1-C4)-alkyl, (C1-C4)-alkylsulfinyl-(C1-C4)-alkyl, (C1-C4)-alkylsulfonyl-(C1-C4)-alkyl, (C1-C6)-alkylcarbonyl, (C1-C6)-haloalkylcarbonyl, (C3-C6)-cycloalkylcarbonyl, (C1-C6)-alkoxycarbonyl, (C1-C6)-haloalkoxycarbonyl, (C3-C6)-cycloalkoxycarbonyl, (C1-C6)-alkylaminocarbonyl, (C2-C8)-dialkylaminocarbonyl, (C3-C6)-cycloalkylaminocarbonyl, (C1-C6)-alkoxy, (C1-C6)-alkylthio, (C1-C6)-haloalkylthio, (C3-C6)-cycloalkylthio,
    • or
    • R4 and R5 together form a 3- to 6-membered carbocyclic ring or a 3- to 6-membered saturated heterocyclic ring having up to 2 oxygen atoms,
    • or
    • R4 and R5 together form a (C1-C3)-alkylidene radical or (C1-C3)-haloalkylidene radical,
    • R6 represents hydrogen, (C1-C6)-alkyl, (C1-C6)-haloalkyl, aryl-(C1-C4)-alkyl, heteroaryl-(C1-C4)-alkyl, (C3-C6)-cycloalkyl, (C3-C6)-cycloalkyl-(C1-C4)-alkyl, (C3-C6)-halocycloalkyl, (C3-C6)-halocycloalkyl-(C1-C4)-alkyl, (C2-C6)-alkenyl, (C2-C6)-alkynyl, (C1-C4)-alkoxy-(C1-C4)-alkyl, (C1-C4)-haloalkoxy-(C1-C4)-alkyl, (C1-C4)-alkylthio-(C1-C4)-alkyl, (C1-C4)-alkylsulfinyl-(C1-C4)-alkyl, (C1-C4)-alkylsulfonyl-(C1-C4)-alkyl, (C1-C6)-alkylcarbonyl, (C1-C6)-haloalkylcarbonyl, (C3-C6)-cycloalkylcarbonyl, formyl, (C1-C6)-alkoxycarbonyl, (C1-C6)-haloalkoxycarbonyl, (C3-C6)-cycloalkoxycarbonyl, (C1-C6)-alkylaminocarbonyl, (C2-C8)-dialkylaminocarbonyl, (C3-C8)-cycloalkylaminocarbonyl,
    • and
    • R7 represents hydrogen, halogen, cyano, nitro, formyl, (C1-C6)-alkyl, (C1-C6)-haloalkyl, (C2-C6)-alkenyl, (C2-C6)-alkynyl, (C2-C6)-haloalkenyl, (C2-C6)-haloalkynyl, (C1-C4)-alkoxy-(C1-C4)-alkyl, (C1-C4)-haloalkoxy-(C1-C4)-alkyl, (C1-C4)-alkylthio-(C1-C4)-alkyl, (C1-C4)-alkylsulfinyl-(C1-C4)-alkyl, (C1-C4)-alkylsulfonyl-(C1-C4)-alkyl, (C1-C6)-alkylcarbonyl, (C1-C8)-haloalkylcarbonyl, (C3-C6)-cycloalkylcarbonyl, carboxyl, (C1-C6)-alkoxycarbonyl, (C1-C6)-haloalkoxycarbonyl, (C3-C6)-cycloalkoxycarbonyl, (C1-C6)-alkylaminocarbonyl, (C2-C8)-dialkylaminocarbonyl, (C3-C6)-cycloalkylaminocarbonyl, hydroxy, (C1-C6)-alkoxy, (C1-C6)-haloalkoxy, (C1-C6)-alkylthio, (C1-C6)-haloalkylthio, (C3-C6)-cycloalkylthio, (C1-C6)-alkylsulfinyl, (C1-C6)-haloalkylsulfinyl, (C3-C6)-cycloalkylsulfinyl, (C1-C6)-alkylsulfonyl, (C1-C6)-haloalkylsulfonyl, (C3-C6)-cycloalkylsulfonyl, (C1-C6)-alkylaminosulfonyl, (C2-C8)-dialkylaminosulfonyl or (C3-C8)-trialkylsilyl.

The invention particularly preferably provides compounds of the general formula (I) in which

    • X represents nitrogen, —CF— or —CH—,
    • A represents oxygen, —S(O)n—, —C(R4)(R5)—, —C(═O)— or —NR6—
    • with n=0, 1 or 2,
    • R1 represents optionally substituted aryl, heteroaryl or heterocyclyl, where each ring or each ring system is optionally substituted by up to 5 substituents independently selected from the group R7,
    • R2 independently of the others represents halogen, cyano, nitro, formyl, formamid, (C1-C4)-alkyl, (C1-C4)-haloalkyl, (C2-C4)-alkenyl, (C2-C4)-alkynyl, (C2-C4)-haloalkenyl, (C1-C4)-alkoxy-(C1-C4)-alkyl, (C1-C4)-haloalkoxy-(C1-C4)-alkyl, (C1-C4)-alkylcarbonyl, (C1-C4)-haloalkylcarbonyl, carboxyl, (C1-C4)-alkoxycarbonyl, (C1-C4)-haloalkoxycarbonyl, (C3-C6)-cycloalkoxycarbonyl, carbamoyl, (C2-C4)-alkylaminocarbonyl, (C2-C6)-dialkylaminocarbonyl, (C1-C4)-alkoxycarbonyl-(C1-C4)-alkyl, (C1-C4)-haloalkoxycarbonyl-(C1-C4)-alkyl, carboxy-(C1-C4)-alkyl, hydroxy, amino, (C1-C4)-alkoxy, (C1-C4)-haloalkoxy, (C1-C4)-alkylthio, (C1-C4)-alkylsulfinyl, (C1-C4)-alkylsulfonyl, (C1-C4)-alkylaminosulfonyl, (C2-C6)-dialkylaminosulfonyl or (C3-C6)-trialkylsilyl,
    • m represents 0, 1, 2 or 3,
    • R3 represents hydrogen, halogen, cyano, nitro, formyl, (C1-C4)-alkyl, (C1-C4)-haloalkyl, (C2-C4)-alkenyl, (C2-C4)-alkynyl, (C2-C4)-haloalkenyl, (C2-C4)-haloalkynyl, (C1-C4)-alkylcarbonyl, (C1-C4)-haloalkylcarbonyl, carboxyl, (C1-C4)-alkoxycarbonyl, (C1-C4)-haloalkoxycarbonyl, (C3-C6)-cycloalkoxycarbonyl, (C1-C4)-alkylaminocarbonyl, (C2-C6)-dialkylaminocarbonyl, hydroxy, (C1-C4)-alkoxy, (C1-C4)-haloalkoxy, (C1-C4)-alkylthio, (C1-C4)-haloalkylthio, (C1-C4)-alkylsulfinyl, (C1-C4)-haloalkylsulfinyl, (C1-C4)-alkylsulfonyl, (C1-C4)-haloalkylsulfonyl, (C1-C4)-alkylaminosulfonyl, (C2-C6)-dialkylaminosulfonyl or (C3-C6)-trialkylsilyl,
    • R4 and R5 independently of one another represent hydrogen, hydroxy, halogen, (C1-C4)-alkyl, (C1-C4)-haloalkyl, (C2-C4)-alkenyl, (C2-C4)-alkynyl, (C1-C4)-alkoxycarbonyl, (C1-C4)-haloalkoxycarbonyl or (C3-C6)-cycloalkoxycarbonyl,
    • or
    • R4 and R5 together form a (C1-C3)-alkylidene radical or (C1-C3)-haloalkylidene radical,
    • R6 represents hydrogen, (C1-C4)-alkyl, (C1-C4)-haloalkyl, aryl-(C1-C4)-alkyl, heteroaryl-(C1-C4)-alkyl, (C2-C4)-alkenyl, (C2-C4)-alkynyl, (C1-C4)-alkylcarbonyl, formyl or (C1-C4)-alkoxycarbonyl,
    • and
    • R7 represents hydrogen, halogen, cyano, nitro, formyl, (C1-C4)-alkyl, (C1-C4)-haloalkyl, (C2-C4)-alkenyl, (C2-C4)-alkynyl, (C2-C4)-haloalkenyl, (C2-C4)-haloalkynyl, (C1-C4)-alkoxy-(C1-C4)-alkyl, (C1-C4)-haloalkoxy-(C1-C4)-alkyl, (C1-C4)-alkylcarbonyl, (C1-C4)-haloalkylcarbonyl, carboxyl, (C1-C4)-alkoxycarbonyl, (C1-C4)-haloalkoxycarbonyl, (C3-C6)-cycloalkoxycarbonyl, (C1-C4)-alkylaminocarbonyl, (C2-C6)-dialkylaminocarbonyl, (C3-C6)-cycloalkylaminocarbonyl, hydroxy, (C1-C4)-alkoxy, (C1-C4)-haloalkoxy, (C1-C4)-alkylthio, (C1-C4)-haloalkylthio, (C1-C4)-alkylsulfinyl, (C1-C4)-haloalkylsulfinyl, (C1-C4)-alkylsulfonyl, (C1-C4)-haloalkylsulfonyl, (C1-C4)-alkylaminosulfonyl, (C2-C6)-dialkylaminosulfonyl or (C3-C6)-trialkylsilyl.

The invention very particularly preferably provides compounds of the general formula (I) in which

    • X represents nitrogen, —CF— or —CH—,
    • A represents oxygen, —S(O)n—, —C(R4)(R5)—, —C(═O)— or —NR6—
    • with n=0, 1 or 2,
    • R1 represents optionally substituted phenyl, pyridyl or pyrimidyl, where each ring or each ring system is optionally substituted by up to 5 substituents independently selected from the group R7,
    • R2 independently of the others represents halogen, cyano, (C1-C4)-alkyl, (C1-C4)-haloalkyl, carboxyl, (C1-C4)-alkoxycarbonyl, (C1-C4)-alkoxycarbonyl-(C1-C3)-alkyl, (C1-C4)-haloalkoxycarbonyl-(C1-C3)-alkyl, carboxy-(C1-C3)-alkyl or (C1-C4)-alkoxy,
    • m represents 0, 1, 2 or 3,
    • R3 represents hydrogen, halogen, cyano, (C1-C4)-alkyl, (C1-C4)-haloalkyl, (C2-C4)-alkenyl, (C2-C4)-alkynyl, (C2-C4)-haloalkenyl, (C2-C4)-haloalkynyl, (C1-C4)-alkoxy or (C1-C4)-haloalkoxy,
    • R4 and R5 independently of one another represent hydrogen, halogen, (C1-C4)-alkyl or (C1-C4)-alkoxycarbonyl,
    • R6 represents hydrogen, (C1-C4)-alkyl, (C1-C4)-alkylcarbonyl or (C1-C4)-alkoxycarbonyl,
    • and
    • R7 represents hydrogen, halogen, cyano, (C1-C4)-alkyl, (C1-C4)-haloalkyl, carboxyl, (C1-C4)-alkoxycarbonyl, hydroxy, (C1-C4)-alkoxy or (C1-C4)-haloalkoxy.

The invention likewise further preferably provides compounds of the general formula (I) in which

    • X represents nitrogen, —CF— or —CH—,
    • A represents oxygen, sulfur, —CH2— or —NR6—,
    • R1 represents optionally substituted phenyl, pyridyl or pyrimidyl, where each ring or each ring system is optionally substituted by up to 5 substituents independently selected from the group R7,
    • R2 independently of the others represents halogen, cyano, (C1-C4)-alkyl, (C1-C4)-haloalkyl, carboxyl, (C1-C4)-alkoxycarbonyl, (C1-C4)-alkoxycarbonyl-(C1-C3)-alkyl, (C1-C4)-haloalkoxycarbonyl-(C1-C3)-alkyl, carboxy-(C1-C3)-alkyl or (C1-C4)-alkoxy,
    • m represents 0, 1, 2 or 3,
    • R3 represents hydrogen, halogen, cyano, (C1-C4)-alkyl, (C1-C4)-haloalkyl, (C1-C4)-alkoxy or (C1-C4)-haloalkoxy,
    • R6 represents hydrogen or methyl,
    • and
    • R7 represents hydrogen, halogen, cyano, (C1-C4)-alkyl, (C1-C4)-haloalkyl, (C1-C4)-alkoxy or (C1-C4)-haloalkoxy.

The invention likewise further preferably provides compounds of the general formula (I) in which

    • X represents —CH—, —CF— or nitrogen,
    • A represents oxygen, sulfur, —CH2— or —NR6—,
    • R1 represents optionally substituted phenyl, pyrid-2-yl or pyrimid-2-yl, where each ring is optionally substituted by up to 5 substituents independently of one another selected from the group R7,
    • R2 independently of the others represents fluorine, chlorine, bromine, cyano, methyl, ethyl, trifluoromethyl, methoxy, methoxycarbonylmethyl, carboxylmethyl,
    • m represents 0, 1, 2 or 3,
    • R3 represents hydrogen, fluorine, chlorine, cyano, methyl, trifluoromethyl, methoxy, trifluoromethoxy,
    • R6 represents hydrogen or methyl,
    • and
    • R7 represents hydrogen, fluorine, chlorine, bromine, cyano, methyl, trifluoromethyl, methoxy, trifluoromethoxy.

The invention most preferably provides compounds of the general formula (I) in which

    • X represents —CH—, —CF— or nitrogen,
    • A represents oxygen, sulfur, —CH2— or —NH—,
    • R1 represents phenyl, 4-fluorophenyl, 2,4-difluorophenyl, 3,4-difluorophenyl, 3-(trifluoromethyl)phenyl, 3-methoxyphenyl, 3-chlorophenyl, 4-chlorophenyl, 4-cyanophenyl, 4-methylphenyl, 3-fluoro-4-methylphenyl, 4-fluoro-3-methylphenyl, 2,4-difluoro-3-methoxyphenyl, 5-chloro-3-fluoropyrid-2-yl, 5-chloropyrid-2-yl, 5-fluoropyrid-2-yl, 3,5-difluoropyrid-2-yl, 5-fluoropyrimid-2-yl, 5-chloropyrimid-2-yl;
    • R2 represents methyl,
    • m represents 0, 1 or 2,
    • and
    • R3 represents hydrogen, fluorine, chlorine, trifluoromethyl.

The definitions of radicals listed above in general terms or within areas of preference apply both to the end products of the general formula (I) and correspondingly to the starting materials or intermediates required for preparation in each case. These radical definitions can be combined with one another as desired, i.e. including combinations between the given preferred ranges.

Primarily for reasons of higher herbicidal activity, better selectivity and/or better producibility, inventive compounds of the abovementioned general formula (I) or their salts or their use according to the invention are of particular interest in which individual radicals have one of the preferred meanings already specified or specified below, or in particular those in which one or more of the preferred meanings already specified or specified below occur in combination.

With regard to the compounds according to the invention, the terms used above and further below will be elucidated. These are familiar to the person skilled in the art and especially have the definitions elucidated hereinafter:

Unless defined differently, names of chemical groups are generally to be understood such that attachment to the skeleton or the remainder of the molecule is via the structural element of the relevant chemical group mentioned last, i.e. for example in the case of (C2-C8)-alkenyloxy via the oxygen atom and in the case of heterocyclyl-(C1-C8)-alkyl or R12O(O)C—(C1-C8)-alkyl in each case via the carbon atom of the alkyl group.

According to the invention, “alkylsulfonyl”—alone or as part of a chemical group—refers to straight-chain or branched alkylsulfonyl, preferably having 1 to 8 or 1 to 6 carbon atoms, for example (but not limited to) (C1-C6)-alkylsulfonyl such as methylsulfonyl, ethylsulfonyl, propylsulfonyl, 1-methylethylsulfonyl, butylsulfonyl, 1-methylpropylsulfonyl, 2-methylpropylsulfonyl, 1,1-dimethylethylsulfonyl, pentylsulfonyl, 1-methylbutylsulfonyl, 2-methylbutylsulfonyl, 3-methylbutylsulfonyl, 1,1-dimethylpropylsulfonyl, 1,2-dimethylpropylsulfonyl, 2,2-dimethylpropylsulfonyl, 1-ethylpropylsulfonyl, hexylsulfonyl, 1-methylpentylsulfonyl, 2-methylpentylsulfonyl, 3-methylpentylsulfonyl, 4-methylpentylsulfonyl, 1,1-dimethylbutylsulfonyl, 1,2-dimethylbutylsulfonyl, 1,3-dimethylbutylsulfonyl, 2,2-dimethylbutylsulfonyl, 2,3-dimethylbutylsulfonyl, 3,3-dimethylbutylsulfonyl, 1-ethylbutylsulfonyl, 2-ethylbutylsulfonyl, 1,1,2-trimethylpropylsulfonyl, 1,2,2-trimethylpropylsulfonyl, 1-ethyl-1-methylpropylsulfonyl and 1-ethyl-2-methylpropylsulfonyl.

According to the invention, “alkylthio”—alone or as part of a chemical group—denotes straight-chain or branched S-alkyl, preferably having 1 to 8 or 1 to 6 carbon atoms, such as (C1-C10)-, (C1-C6)- or (C1-C4)-alkylthio, for example (but not limited to) (C1-C6)-alkylthio such as methylthio, ethylthio, propylthio, 1-methylethylthio, butylthio, 1-methylpropylthio, 2-methylpropylthio, 1,1-dimethylethylthio, pentylthio, 1-methylbutylthio, 2-methylbutylthio, 3-methylbutylthio, 1,1-dimethylpropylthio, 1,2-dimethylpropylthio, 2,2-dimethylpropylthio, 1-ethylpropylthio, hexylthio, 1-methylpentylthio, 2-methylpentylthio, 3-methylpentylthio, 4-methylpentylthio, 1,1-dimethylbutylthio, 1,2-dimethylbutylthio, 1,3-dimethylbutylthio, 2,2-dimethylbutylthio, 2,3-dimethylbutylthio, 3,3-dimethylbutylthio, 1-ethylbutylthio, 2-ethylbutylthio, 1,1,2-trimethylpropylthio, 1,2,2-trimethylpropylthio, 1-ethyl-1-methylpropylthio and 1-ethyl-2-methylpropylthio.

According to the invention, “alkylsulfinyl (alkyl-S(═O)—)”, unless defined differently elsewhere, denotes alkyl radicals which are bonded to the skeleton via —S(═O)—, such as (C1-C10)-, (C1-C6)- or (C1-C4)-alkylsulfinyl, for example (but not limited to) (C1-C6)-alkylsulfinyl such as methylsulfinyl, ethylsulfinyl, propylsulfinyl, 1-methylethylsulfinyl, butylsulfinyl, 1-methylpropylsulfinyl, 2-methylpropylsulfinyl, 1,1-dimethylethylsulfinyl, pentylsulfinyl, 1-methylbutylsulfinyl, 2-methylbutylsulfinyl, 3-methylbutylsulfinyl, 1,1-dimethylpropylsulfinyl, 1,2-dimethylpropylsulfinyl, 2,2-dimethylpropylsulfinyl, 1-ethylpropylsulfinyl, hexylsulfinyl, 1-methylpentylsulfinyl, 2-methylpentylsulfinyl, 3-methylpentylsulfinyl, 4-methylpentylsulfinyl, 1,1-dimethylbutylsulfinyl, 1,2-dimethylbutylsulfinyl, 1,3-dimethylbutylsulfinyl, 2,2-dimethylbutylsulfinyl, 2,3-dimethylbutylsulfinyl, 3,3-dimethylbutylsulfinyl, 1-ethylbutylsulfinyl, 2-ethylbutylsulfinyl, 1,1,2-trimethylpropylsulfinyl, 1,2,2-trimethylpropylsulfinyl, 1-ethyl-1-methylpropylsulfinyl and 1-ethyl-2-methylpropylsulfinyl.

“Alkoxy” denotes an alkyl radical bonded via an oxygen atom, for example (but not limited to) (C1-C6)-alkoxy such as methoxy, ethoxy, propoxy, 1-methylethoxy, butoxy, 1-methylpropoxy, 2-methylpropoxy, 1,1-dimethylethoxy, pentoxy, 1-methylbutoxy, 2-methylbutoxy, 3-methylbutoxy, 1,1-dimethylpropoxy, 1,2-dimethylpropoxy, 2,2-dimethylpropoxy, 1-ethylpropoxy, hexoxy, 1-methylpentoxy, 2-methylpentoxy, 3-methylpentoxy, 4-methylpentoxy, 1,1-dimethylbutoxy, 1,2-dimethylbutoxy, 1,3-dimethylbutoxy, 2,2-dimethylbutoxy, 2,3-dimethylbutoxy, 3,3-dimethylbutoxy, 1-ethylbutoxy, 2-ethylbutoxy, 1,1,2-trimethylpropoxy, 1,2,2-trimethylpropoxy, 1-ethyl-1-methylpropoxy and 1-ethyl-2-methylpropoxy. Alkenyloxy denotes an alkenyl radical bonded via an oxygen atom, and alkynyloxy denotes an alkynyl radical bonded via an oxygen atom, such as (C2-C10)-, (C2-C6)- or (C2-C4)-alkenoxy and (C3-C10)-, (C3-C6)- or (C3-C4)-alkynoxy.

According to the invention, “alkylcarbonyl” (alkyl-C(═O)—), unless defined differently elsewhere, represents alkyl radicals bonded to the skeleton via —C(═O)—, such as (C1-C10)-, (C1-C6)- or (C1-C4)-alkylcarbonyl. Here, the number of the carbon atoms refers to the alkyl radical in the alkylcarbonyl group.

“Alkoxycarbonyl (alkyl-O—C(═O)—)”, unless defined differently elsewhere: alkyl radicals bonded to the skeleton via —O—C(═O)—, such as (C1-C10)-, (C1-C6)- or (C1-C4)-alkoxycarbonyl. Here, the number of the carbon atoms refers to the alkyl radical in the alkoxycarbonyl group. Analogously, “alkenyloxycarbonyl” and “alkynyloxycarbonyl”, unless defined differently elsewhere, in accordance with the invention, respectively represent alkenyl and alkynyl radicals bonded to the skeleton via —O—C(═O)—, such as (C2-C10)-, (C2-C6)- or (C2-C4)-alkenyloxycarbonyl and (C3-C10)-, (C3-C6)- or (C3-C4)-alkynyloxycarbonyl. Here, the number of the carbon atoms refers to the alkenyl or alkynyl radical in the alkenoxycarbonyl or alkynyloxycarbonyl group.

The term “aryl” denotes an optionally substituted mono-, bi- or polycyclic aromatic system having preferably 6 to 14, especially 6 to 10, ring carbon atoms, for example phenyl, naphthyl, anthryl, phenanthrenyl and the like, preferably phenyl.

A heterocyclic radical (heterocyclyl) contains at least one heterocyclic ring (=carbocyclic ring in which at least one carbon atom has been replaced by a heteroatom, preferably by a heteroatom from the group of N, O, S, P) which is saturated or partially saturated and may be unsubstituted or substituted, in which case the bonding site is localized on a ring atom. If the heterocyclyl radical or the heterocyclic ring is optionally substituted, it may be fused to other carbocyclic or heterocyclic rings. In the case of optionally substituted heterocyclyl, polycyclic systems are also included, for example 8-azabicyclo[3.2.1]octanyl, 8-azabicyclo[2.2.2]octanyl or 1-azabicyclo[2.2.1]heptyl. Optionally substituted heterocyclyl also includes spirocyclic systems, such as, for example, 1-oxa-5-azaspiro[2.3]hexyl. Unless defined differently, the heterocyclic ring preferably contains 3 to 9 ring atoms, especially 3 to 6 ring atoms, and one or more, preferably 1 to 4, especially 1, 2 or 3, heteroatoms in the heterocyclic ring, preferably from the group of N, O and S, but no two oxygen atoms should be directly adjacent, for example with one heteroatom from the group of N, O and S: 1- or 2- or 3-pyrrolidinyl, 3,4-dihydro-2H-pyrrol-2- or -3-yl, 2,3-dihydro-1H-pyrrol-1- or -2- or -3- or -4- or -5-yl; 2,5-dihydro-1H-pyrrol-1- or -2- or -3-yl, 1- or 2- or 3- or 4-piperidinyl; 2,3,4,5-tetrahydropyridin-2- or -3- or -4- or -5-yl or -6-yl; 1,2,3,6-tetrahydropyridin-1- or -2- or -3- or -4- or -5- or -6-yl; 1,2,3,4-tetrahydropyridin-1- or -2- or -3- or -4- or -5- or -6-yl; 1,4-dihydropyridin-1- or -2- or -3- or -4-yl; 2,3-dihydropyridin-2- or -3- or -4- or -5- or -6-yl; 2,5-dihydropyridin-2- or -3- or -4- or -5- or -6-yl, 1- or 2- or 3- or 4-azepanyl; 2,3,4,5-tetrahydro-1H-azepin-1- or -2- or -3- or -4- or -5- or -6- or -7-yl; 2,3,4,7-tetrahydro-1H-azepin-1- or -2- or -3- or -4- or -5- or -6- or -7-yl; 2,3,6,7-tetrahydro-1H-azepin-1- or -2- or -3- or -4-yl; 3,4,5,6-tetrahydro-2H-azepin-2- or -3- or -4- or -5- or -6- or -7-yl; 4,5-dihydro-1H-azepin-1- or -2- or -3- or -4-yl; 2,5-dihydro-1H-azepin-1- or -2- or -3- or -4- or -5- or -6- or -7-yl; 2,7-dihydro-1H-azepin-1- or -2- or -3- or -4-yl; 2,3-dihydro-1H-azepin-1- or -2- or -3- or -4- or -5- or -6- or -7-yl; 3,4-dihydro-2H-azepin-2- or -3- or -4- or -5- or -6- or -7-yl; 3,6-dihydro-2H-azepin-2- or -3- or -4- or -5- or -6- or -7-yl; 5,6-dihydro-2H-azepin-2- or -3- or -4- or -5- or -6- or -7-yl; 4,5-dihydro-3H-azepin-2- or -3- or -4- or -5- or -6- or -7-yl; 1H-azepin-1- or -2- or -3- or -4- or -5- or -6- or -7-yl; 2H-azepin-2- or -3- or -4- or -5- or -6- or -7-yl; 3H-azepin-2- or -3- or -4- or -5- or -6- or -7-yl; 4H-azepin-2- or -3- or -4- or -5- or -6- or -7-yl, 2- or 3-oxolanyl (=2- or 3-tetrahydrofuranyl); 2,3-dihydrofuran-2- or -3- or -4- or -5-yl; 2,5-dihydrofuran-2- or -3-yl, 2- or 3- or 4-oxanyl (=2- or 3- or 4-tetrahydropyranyl); 3,4-dihydro-2H-pyran-2- or -3- or -4- or -5- or -6-yl; 3,6-dihydro-2H-pyran-2- or -3- or -4- or -5- or -6-yl; 2H-pyran-2- or -3- or -4- or -5- or -6-yl; 4H-pyran-2- or -3- or -4-yl, 2- or 3- or 4-oxepanyl; 2,3,4,5-tetrahydrooxepin-2- or -3- or -4- or -5- or -6- or -7-yl; 2,3,4,7-tetrahydrooxepin-2- or -3- or -4- or -5- or -6- or -7-yl; 2,3,6,7-tetrahydrooxepin-2- or -3- or -4-yl; 2,3-dihydrooxepin-2- or -3- or -4- or -5- or -6- or -7-yl; 4,5-dihydrooxepin-2- or -3- or -4-yl; 2,5-dihydrooxepin-2- or -3- or -4- or -5- or -6- or -7-yl; oxepin-2- or -3- or -4- or -5- or -6- or -7-yl; 2- or 3-tetrahydrothiophenyl; 2,3-dihydrothiophen-2- or -3- or -4- or -5-yl; 2,5-dihydrothiophen-2- or -3-yl; tetrahydro-2H-thiopyran-2- or -3- or -4-yl; 3,4-dihydro-2H-thiopyran-2- or -3- or -4- or -5- or -6-yl; 3,6-dihydro-2H-thiopyran-2- or -3- or -4- or -5- or -6-yl; 2H-thiopyran-2- or -3- or -4- or -5- or -6-yl; 4H-thiopyran-2- or -3- or -4-yl. Preferred 3-membered and 4-membered heterocycles are, for example, 1- or 2-aziridinyl, oxiranyl, thiiranyl, 1- or 2- or 3-azetidinyl, 2- or 3-oxetanyl, 2- or 3-thietanyl, 1,3-dioxetan-2-yl. Further examples of “heterocyclyl” are a partially or fully hydrogenated heterocyclic radical having two heteroatoms from the group consisting of N, O and S, such as, for example, 1- or 2- or 3- or 4-pyrazolidinyl; 4,5-dihydro-3H-pyrazol-3- or -4- or -5-yl; 4,5-dihydro-1H-pyrazol-1- or -3- or -4- or -5-yl; 2,3-dihydro-1H-pyrazol-1- or -2- or -3- or -4- or -5-yl; 1- or 2- or 3- or 4-imidazolidinyl; 2,3-dihydro-1H-imidazol-1- or -2- or -3- or -4-yl; 2,5-dihydro-1H-imidazol-1- or -2- or -4- or -5-yl; 4,5-dihydro-1H-imidazol-1- or -2- or -4- or -5-yl; hexahydropyridazin-1- or -2- or -3- or -4-yl; 1,2,3,4-tetrahydropyridazin-1- or -2- or -3- or -4- or -5- or -6-yl; 1,2,3,6-tetrahydropyridazin-1- or -2- or -3- or -4- or -5- or -6-yl; 1,4,5,6-tetrahydropyridazin-1- or -3- or -4- or -5- or -6-yl; 3,4,5,6-tetrahydropyridazin-3- or -4- or -5-yl; 4,5-dihydropyridazin-3- or -4-yl; 3,4-dihydropyridazin-3- or -4- or -5- or -6-yl; 3,6-dihydropyridazin-3- or -4-yl; 1,6-dihydropyriazin-1- or -3- or -4- or -5- or -6-yl; hexahydropyrimidin-1- or -2- or -3- or -4-yl; 1,4,5,6-tetrahydropyrimidin-1- or -2- or -4- or -5- or -6-yl; 1,2,5,6-tetrahydropyrimidin-1- or -2- or -4- or -5- or -6-yl; 1,2,3,4-tetrahydropyrimidin-1- or -2- or -3- or -4- or -5- or -6-yl; 1,6-dihydropyrimidin-1- or -2- or -4- or -5- or -6-yl; 1,2-dihydropyrimidin-1- or -2- or -4- or -5- or -6-yl; 2,5-dihydropyrimidin-2- or -4- or -5-yl; 4,5-dihydropyrimidin-4- or -5- or -6-yl; 1,4-dihydropyrimidin-1- or -2- or -4- or -5- or -6-yl; 1- or 2- or 3-piperazinyl; 1,2,3,6-tetrahydropyrazin-1- or -2- or -3- or -5- or -6-yl; 1,2,3,4-tetrahydropyrazin-1- or -2- or -3- or -4- or -5- or -6-yl; 1,2-dihydropyrazin-1- or -2- or -3- or -5- or -6-yl; 1,4-dihydropyrazin-1- or -2- or -3-yl; 2,3-dihydropyrazin-2- or -3- or -5- or -6-yl; 2,5-dihydropyrazin-2- or -3-yl; 1,3-dioxolan-2- or -4- or -5-yl; 1,3-dioxol-2- or -4-yl; 1,3-dioxan-2- or -4- or -5-yl; 4H-1,3-dioxin-2- or -4- or -5- or -6-yl; 1,4-dioxan-2- or -3- or -5- or -6-yl; 2,3-dihydro-1,4-dioxin-2- or -3- or -5- or -6-yl; 1,4-dioxin-2- or -3-yl; 1,2-dithiolan-3- or -4-yl; 3H-1,2-dithiol-3- or -4- or -5-yl; 1,3-dithiolan-2- or -4-yl; 1,3-dithiol-2- or -4-yl; 1,2-dithian-3- or -4-yl; 3,4-dihydro-1,2-dithiin-3- or -4- or -5- or -6-yl; 3,6-dihydro-1,2-dithiin-3- or -4-yl; 1,2-dithiin-3- or -4-yl; 1,3-dithian-2- or -4- or -5-yl; 4H-1,3-dithiin-2- or -4- or -5- or -6-yl; isoxazolidin-2- or -3- or -4- or -5-yl; 2,3-dihydroisoxazol-2- or -3- or -4- or -5-yl; 2,5-dihydroisoxazol-2- or -3- or -4- or -5-yl; 4,5-dihydroisoxazol-3- or -4- or -5-yl; 1,3-oxazolidin-2- or -3- or -4- or -5-yl; 2,3-dihydro-1,3-oxazol-2- or -3- or -4- or -5-yl; 2,5-dihydro-1,3-oxazol-2- or -4- or -5-yl; 4,5-dihydro-1,3-oxazol-2- or -4- or -5-yl; 1,2-oxazinan-2- or -3- or -4- or -5- or -6-yl; 3,4-dihydro-2H-1,2-oxazin-2- or -3- or -4- or -5- or -6-yl; 3,6-dihydro-2H-1,2-oxazin-2- or -3- or -4- or -5- or -6-yl; 5,6-dihydro-2H-1,2-oxazin-2- or -3- or -4- or -5- or -6-yl; 5,6-dihydro-4H-1,2-oxazin-3- or -4- or -5- or -6-yl; 2H-1,2-oxazin-2- or -3- or -4- or -5- or -6-yl; 6H-1,2-oxazin-3- or -4- or -5- or -6-yl; 4H-1,2-oxazin-3- or -4- or -5- or -6-yl; 1,3-oxazinan-2- or -3- or -4- or -5- or -6-yl; 3,4-dihydro-2H-1,3-oxazin-2- or -3- or -4- or -5- or -6-yl; 3,6-dihydro-2H-1,3-oxazin-2- or -3- or -4- or -5- or -6-yl; 5,6-dihydro-2H-1,3-oxazin-2- or -4- or -5- or -6-yl; 5,6-dihydro-4H-1,3-oxazin-2- or -4- or -5- or -6-yl; 2H-1,3-oxazin-2- or -4- or -5- or -6-yl; 6H-1,3-oxazin-2- or -4- or -5- or -6-yl; 4H-1,3-oxazin-2- or -4- or -5- or -6-yl; morpholin-2- or -3- or -4-yl; 3,4-dihydro-2H-1,4-oxazin-2- or -3- or -4- or -5- or -6-yl; 3,6-dihydro-2H-1,4-oxazin-2- or -3- or -5- or -6-yl; 2H-1,4-oxazin-2- or -3- or -5- or -6-yl; 4H-1,4-oxazin-2- or -3-yl; 1,2-oxazepan-2- or -3- or -4- or -5- or -6- or -7-yl; 2,3,4,5-tetrahydro-1,2-oxazepin-2- or -3- or -4- or -5- or -6- or -7-yl; 2,3,4,7-tetrahydro-1,2-oxazepin-2- or -3- or -4- or -5- or -6- or -7-yl; 2,3,6,7-tetrahydro-1,2-oxazepin-2- or -3- or -4- or -5- or -6- or -7-yl; 2,5,6,7-tetrahydro-1,2-oxazepin-2- or -3- or -4- or -5- or -6- or -7-yl; 4,5,6,7-tetrahydro-1,2-oxazepin-3- or -4- or -5- or -6- or -7-yl; 2,3-dihydro-1,2-oxazepin-2- or -3- or -4- or -5- or -6- or -7-yl; 2,5-dihydro-1,2-oxazepin-2- or -3- or -4- or -5- or -6- or -7-yl; 2,7-dihydro-1,2-oxazepin-2- or -3- or -4- or -5- or -6- or -7-yl; 4,5-dihydro-1,2-oxazepin-3- or -4- or -5- or -6- or -7-yl; 4,7-dihydro-1,2-oxazepin-3- or -4- or -5- or -6- or -7-yl; 6,7-dihydro-1,2-oxazepin-3- or -4- or -5- or -6- or -7-yl; 1,2-oxazepin-3- or -4- or -5- or -6- or -7-yl; 1,3-oxazepan-2- or -3- or -4- or -5- or -6- or -7-yl; 2,3,4,5-tetrahydro-1,3-oxazepin-2- or -3- or -4- or -5- or -6- or -7-yl; 2,3,4,7-tetrahydro-1,3-oxazepin-2- or -3- or -4- or -5- or -6- or -7-yl; 2,3,6,7-tetrahydro-1,3-oxazepin-2- or -3- or -4- or -5- or -6- or -7-yl; 2,5,6,7-tetrahydro-1,3-oxazepin-2- or -4- or -5- or -6- or -7-yl; 4,5,6,7-tetrahydro-1,3-oxazepin-2- or -4- or -5- or -6- or -7-yl; 2,3-dihydro-1,3-oxazepin-2- or -3- or -4- or -5- or -6- or -7-yl; 2,5-dihydro-1,3-oxazepin-2- or -4- or -5- or -6- or -7-yl; 2,7-dihydro-1,3-oxazepin-2- or -4- or -5- or -6- or -7-yl; 4,5-dihydro-1,3-oxazepin-2- or -4- or -5- or -6- or -7-yl; 4,7-dihydro-1,3-oxazepin-2- or -4- or -5- or -6- or -7-yl; 6,7-dihydro-1,3-oxazepin-2- or -4- or -5- or -6- or -7-yl; 1,3-oxazepin-2- or -4- or -5- or -6- or -7-yl; 1,4-oxazepan-2- or -3- or -5- or -6- or -7-yl; 2,3,4,5-tetrahydro-1,4-oxazepin-2- or -3- or -4- or -5- or -6- or -7-yl; 2,3,4,7-tetrahydro-1,4-oxazepin-2- or -3- or -4- or -5- or -6- or -7-yl; 2,3,6,7-tetrahydro-1,4-oxazepin-2- or -3- or -5- or -6- or -7-yl; 2,5,6,7-tetrahydro-1,4-oxazepin-2- or -3- or -5- or -6- or -7-yl; 4,5,6,7-tetrahydro-1,4-oxazepin-2- or -3- or -4- or -5- or -6- or -7-yl; 2,3-dihydro-1,4-oxazepin-2- or -3- or -5- or -6- or -7-yl; 2,5-dihydro-1,4-oxazepin-2- or -3- or -5- or -6- or -7-yl; 2,7-dihydro-1,4-oxazepin-2- or -3- or -5- or -6- or -7-yl; 4,5-dihydro-1,4-oxazepin-2- or -3- or -4- or -5- or -6- or -7-yl; 4,7-dihydro-1,4-oxazepin-2- or -3- or -4- or -5- or -6- or -7-yl; 6,7-dihydro-1,4-oxazepin-2- or -3- or -5- or -6- or -7-yl; 1,4-oxazepin-2- or -3- or -5- or -6- or -7-yl; isothiazolidin-2- or -3- or -4- or -5-yl; 2,3-dihydroisothiazol-2- or -3- or -4- or -5-yl; 2,5-dihydroisothiazol-2- or -3- or -4- or -5-yl; 4,5-dihydroisothiazol-3- or -4- or -5-yl; 1,3-thiazolidin-2- or -3- or -4- or -5-yl; 2,3-dihydro-1,3-thiazol-2- or -3- or -4- or -5-yl; 2,5-dihydro-1,3-thiazol-2- or -4- or -5-yl; 4,5-dihydro-1,3-thiazol-2- or -4- or -5-yl; 1,3-thiazinan-2- or -3- or -4- or -5- or -6-yl; 3,4-dihydro-2H-1,3-thiazin-2- or -3- or -4- or -5- or -6-yl; 3,6-dihydro-2H-1,3-thiazin-2- or -3- or -4- or -5- or -6-yl; 5,6-dihydro-2H-1,3-thiazin-2- or -4- or -5- or -6-yl; 5,6-dihydro-4H-1,3-thiazin-2- or -4- or -5- or -6-yl; 2H-1,3-thiazin-2- or -4- or -5- or -6-yl; 6H-1,3-thiazin-2- or -4- or -5- or -6-yl; 4H-1,3-thiazin-2- or -4- or -5- or -6-yl. Further examples of “heterocyclyl” are a partially or fully hydrogenated heterocyclic radical having 3 heteroatoms from the group of N, O and S, for example 1,4,2-dioxazolidin-2- or -3- or -5-yl; 1,4,2-dioxazol-3- or -5-yl; 1,4,2-dioxazinan-2- or -3- or -5- or -6-yl; 5,6-dihydro-1,4,2-dioxazin-3- or -5- or -6-yl; 1,4,2-dioxazin-3- or -5- or -6-yl; 1,4,2-dioxazepan-2- or -3- or -5- or -6- or -7-yl; 6,7-dihydro-5H-1,4,2-dioxazepin-3- or -5- or -6- or -7-yl; 2,3-dihydro-7H-1,4,2-dioxazepin-2- or -3- or -5- or -6- or -7-yl; 2,3-dihydro-5H-1,4,2-dioxazepin-2- or -3- or -5- or -6- or -7-yl; 5H-1,4,2-dioxazepin-3- or -5- or -6- or -7-yl; 7H-1,4,2-dioxazepin-3- or -5- or -6- or -7-yl. Structural examples of heterocycles which are optionally substituted further are also listed below

When a base structure is substituted “by one or more radicals” from a list of radicals (=group) or a generically defined group of radicals, this in each case includes simultaneous substitution by a plurality of identical and/or structurally different radicals.

In the case of a partially or fully saturated nitrogen heterocycle, this may be joined to the remainder of the molecule either via carbon or via the nitrogen.

Suitable substituents for a substituted heterocyclic radical are the substituents specified further down, and additionally also oxo and thioxo. The oxo group as a substituent on a ring carbon atom is then, for example, a carbonyl group in the heterocyclic ring. As a result, lactones and lactams are preferably also included. The oxo group may also occur on the ring heteroatoms, which may exist in different oxidation states, for example in the case of N and S, and in that case form, for example, the divalent —N(O)—, —S(O)— (also SO for short) and —S(O)2— (also SO2 for short) groups in the heterocyclic ring. In the case of —N(O)— and —S(O)— groups, both enantiomers in each case are included.

According to the invention, the expression “heteroaryl” refers to heteroaromatic compounds, i.e. fully unsaturated aromatic heterocyclic compounds, preferably 5- to 7-membered rings having 1 to 4, preferably 1 or 2, identical or different heteroatoms, preferably 0, S or N. Inventive heteroaryls are, for example, 1H-pyrrol-1-yl; 1H-pyrrol-2-yl; 1H-pyrrol-3-yl; furan-2-yl; furan-3-yl; thien-2-yl; thien-3-yl, 1H-imidazol-1-yl; 1H-imidazol-2-yl; 1H-imidazol-4-yl; 1H-imidazol-5-yl; 1H-pyrazol-1-yl; 1H-pyrazol-3-yl; 1H-pyrazol-4-yl; 1H-pyrazol-5-yl, 1H-1,2,3-triazol-1-yl, 1H-1,2,3-triazol-4-yl, 1H-1,2,3-triazol-5-yl, 2H-1,2,3-triazol-2-yl, 2H-1,2,3-triazol-4-yl, 1H-1,2,4-triazol-1-yl, 1H-1,2,4-triazol-3-yl, 4H-1,2,4-triazol-4-yl, 1,2,4-oxadiazol-3-yl, 1,2,4-oxadiazol-5-yl, 1,3,4-oxadiazol-2-yl, 1,2,3-oxadiazol-4-yl, 1,2,3-oxadiazol-5-yl, 1,2,5-oxadiazol-3-yl, azepinyl, pyridin-2-yl, pyridin-3-yl, pyridin-4-yl, pyrazin-2-yl, pyrazin-3-yl, pyrimidin-2-yl, pyrimidin-4-yl, pyrimidin-5-yl, pyridazin-3-yl, pyridazin-4-yl, 1,3,5-triazin-2-yl, 1,2,4-triazin-3-yl, 1,2,4-triazin-5-yl, 1,2,4-triazin-6-yl, 1,2,3-triazin-4-yl, 1,2,3-triazin-5-yl, 1,2,4-, 1,3,2-, 1,3,6- and 1,2,6-oxazinyl, isoxazol-3-yl, isoxazol-4-yl, isoxazol-5-yl, 1,3-oxazol-2-yl, 1,3-oxazol-4-yl, 1,3-oxazol-5-yl, isothiazol-3-yl, isothiazol-4-yl, isothiazol-5-yl, 1,3-thiazol-2-yl, 1,3-thiazol-4-yl, 1,3-thiazol-5-yl, oxepinyl, thiepinyl, 1,2,4-triazolonyl and 1,2,4-diazepinyl, 2H-1,2,3,4-tetrazol-5-yl, 1H-1,2,3,4-tetrazol-5-yl, 1,2,3,4-oxatriazol-5-yl, 1,2,3,4-thiatriazol-5-yl, 1,2,3,5-oxatriazol-4-yl, 1,2,3,5-thiatriazol-4-yl. The heteroaryl groups according to the invention may also be substituted by one or more identical or different radicals. If two adjacent carbon atoms are part of a further aromatic ring, the systems are fused heteroaromatic systems, such as benzofused or polyannelated heteroaromatics. Preferred examples are quinolines (e.g. quinolin-2-yl, quinolin-3-yl, quinolin-4-yl, quinolin-5-yl, quinolin-6-yl, quinolin-7-yl, quinolin-8-yl); isoquinolines (e.g. isoquinolin-1-yl, isoquinolin-3-yl, isoquinolin-4-yl, isoquinolin-5-yl, isoquinolin-6-yl, isoquinolin-7-yl, isoquinolin-8-yl); quinoxaline; quinazoline; cinnoline; 1,5-naphthyridine; 1,6-naphthyridine; 1,7-naphthyridine; 1,8-naphthyridine; 2,6-naphthyridine; 2,7-naphthyridine; phthalazine; pyridopyrazines; pyridopyrimidines; pyridopyridazines; pteridines; pyrimidopyrimidines. Examples of heteroaryl are also 5- or 6-membered benzofused rings from the group of 1H-indol-1-yl, 1H-indol-2-yl, 1H-indol-3-yl, 1H-indol-4-yl, 1H-indol-5-yl, 1H-indol-6-yl, 1H-indol-7-yl, 1-benzofuran-2-yl, 1-benzofuran-3-yl, 1-benzofuran-4-yl, 1-benzofuran-5-yl, 1-benzofuran-6-yl, 1-benzofuran-7-yl, 1-benzothiophen-2-yl, 1-benzothiophen-3-yl, 1-benzothiophen-4-yl, 1-benzothiophen-5-yl, 1-benzothiophen-6-yl, 1-benzothiophen-7-yl, 1H-indazol-1-yl, 1H-indazol-3-yl, 1H-indazol-4-yl, 1H-indazol-5-yl, 1H-indazol-6-yl, 1H-indazol-7-yl, 2H-indazol-2-yl, 2H-indazol-3-yl, 2H-indazol-4-yl, 2H-indazol-5-yl, 2H-indazol-6-yl, 2H-indazol-7-yl, 2H-isoindol-2-yl, 2H-isoindol-1-yl, 2H-isoindol-3-yl, 2H-isoindol-4-yl, 2H-isoindol-5-yl, 2H-isoindol-6-yl; 2H-isoindol-7-yl, 1H-benzimidazol-1-yl, 1H-benzimidazol-2-yl, 1H-benzimidazol-4-yl, 1H-benzimidazol-5-yl, 1H-benzimidazol-6-yl, 1H-benzimidazol-7-yl, 1,3-benzoxazol-2-yl, 1,3-benzoxazol-4-yl, 1,3-benzoxazol-5-yl, 1,3-benzoxazol-6-yl, 1,3-benzoxazol-7-yl, 1,3-benzothiazol-2-yl, 1,3-benzothiazol-4-yl, 1,3-benzothiazol-5-yl, 1,3-benzothiazol-6-yl, 1,3-benzothiazol-7-yl, 1,2-benzisoxazol-3-yl, 1,2-benzisoxazol-4-yl, 1,2-benzisoxazol-5-yl, 1,2-benzisoxazol-6-yl, 1,2-benzisoxazol-7-yl, 1,2-benzisothiazol-3-yl, 1,2-benzisothiazol-4-yl, 1,2-benzisothiazol-5-yl, 1,2-benzisothiazol-6-yl, 1,2-benzisothiazol-7-yl.

The term “halogen” denotes, for example, fluorine, chlorine, bromine or iodine. If the term is used for a radical, “halogen” denotes, for example, a fluorine, chlorine, bromine or iodine atom.

According to the invention, “alkyl” means a straight-chain or branched open-chain, saturated hydrocarbon radical which is optionally mono- or polysubstituted, and in the latter case is referred to as “substituted alkyl”. Preferred substituents are halogen atoms, alkoxy, haloalkoxy, cyano, alkylthio, haloalkylthio, amino or nitro groups, particular preference being given to methoxy, methyl, fluoroalkyl, cyano, nitro, fluorine, chlorine, bromine or iodine. The prefix “bis” also includes the combination of different alkyl radicals, e.g. methyl(ethyl) or ethyl(methyl).

“Haloalkyl”, “-alkenyl” and “-alkynyl” respectively denote alkyl, alkenyl and alkynyl partially or fully substituted by identical or different halogen atoms, for example monohaloalkyl such as CH2CH2Cl, CH2CH2Br, CHClCH3, CH2Cl, CH2F; perhaloalkyl such as CCl3, CClF2, CFCl2, CF2CClF2, CF2CClFCF3; polyhaloalkyl such as CH2CHFCl, CF2CClFH, CF2CBrFH, CH2CF3; the term perhaloalkyl also encompasses the term perfluoroalkyl.

“Haloalkoxy” is, for example, OCF3, OCHF2, OCH2F, OCF2CF3, OCH2CF3 and OCH2CH2Cl; this applies correspondingly to haloalkenyl and other halogen-substituted radicals.

The expression “(C1-C4)-alkyl” mentioned here by way of example is a brief notation for straight-chain or branched alkyl having one to 4 carbon atoms according to the range stated for carbon atoms, i.e. encompasses the methyl, ethyl, 1-propyl, 2-propyl, 1-butyl, 2-butyl, 2-methylpropyl or tert-butyl radicals. General alkyl radicals with a larger specified range of carbon atoms, e.g. “(C1-C6)-alkyl”, correspondingly also encompass straight-chain or branched alkyl radicals with a greater number of carbon atoms, i.e. according to the example also the alkyl radicals having 5 and 6 carbon atoms.

Unless stated specifically, preference is given to the lower carbon skeletons, for example having from 1 to 6 carbon atoms, or having from 2 to 6 carbon atoms in the case of unsaturated groups, in the case of the hydrocarbyl radicals such as alkyl, alkenyl and alkynyl radicals, including in composite radicals. Alkyl radicals, including in composite radicals such as alkoxy, haloalkyl, etc., are, for example, methyl, ethyl, n-propyl or i-propyl, n-, i-, t- or 2-butyl, pentyls, hexyls such as n-hexyl, i-hexyl and 1,3-dimethylbutyl, heptyls such as n-heptyl, 1-methylhexyl and 1,4-dimethylpentyl; alkenyl and alkynyl radicals are defined as the possible unsaturated radicals corresponding to the alkyl radicals, where at least one double bond or triple bond is present. Preference is given to radicals having one double bond or triple bond.

The term “alkenyl” also includes, in particular, straight-chain or branched open-chain hydrocarbon radicals having more than one double bond, such as 1,3-butadienyl and 1,4-pentadienyl, but also allenyl or cumulenyl radicals having one or more cumulated double bonds, for example allenyl (1,2-propadienyl), 1,2-butadienyl and 1,2,3-pentatrienyl. Alkenyl denotes, for example, vinyl which may optionally be substituted by further alkyl radicals, for example (but not limited thereto) (C2-C6)-alkenyl such as ethenyl, 1-propenyl, 2-propenyl, 1-methylethenyl, 1-butenyl, 2-butenyl, 3-butenyl, 1-methyl-1-propenyl, 2-methyl-1-propenyl, 1-methyl-2-propenyl, 2-methyl-2-propenyl, 1-pentenyl, 2-pentenyl, 3-pentenyl, 4-pentenyl, 1-methyl-1-butenyl, 2-methyl-1-butenyl, 3-methyl-1-butenyl, 1-methyl-2-butenyl, 2-methyl-2-butenyl, 3-methyl-2-butenyl, 1-methyl-3-butenyl, 2-methyl-3-butenyl, 3-methyl-3-butenyl, 1,1-dimethyl-2-propenyl, 1,2-dimethyl-1-propenyl, 1,2-dimethyl-2-propenyl, 1-ethyl-1-propenyl, 1-ethyl-2-propenyl, 1-hexenyl, 2-hexenyl, 3-hexenyl, 4-hexenyl, 5-hexenyl, 1-methyl-1-pentenyl, 2-methyl-1-pentenyl, 3-methyl-1-pentenyl, 4-methyl-1-pentenyl, 1-methyl-2-pentenyl, 2-methyl-2-pentenyl, 3-methyl-2-pentenyl, 4-methyl-2-pentenyl, 1-methyl-3-pentenyl, 2-methyl-3-pentenyl, 3-methyl-3-pentenyl, 4-methyl-3-pentenyl, 1-methyl-4-pentenyl, 2-methyl-4-pentenyl, 3-methyl-4-pentenyl, 4-methyl-4-pentenyl, 1,1-dimethyl-2-butenyl, 1,1-dimethyl-3-butenyl, 1,2-dimethyl-1-butenyl, 1,2-dimethyl-2-butenyl, 1,2-dimethyl-3-butenyl, 1,3-dimethyl-1-butenyl, 1,3-dimethyl-2-butenyl, 1,3-dimethyl-3-butenyl, 2,2-dimethyl-3-butenyl, 2,3-dimethyl-1-butenyl, 2,3-dimethyl-2-butenyl, 2,3-dimethyl-3-butenyl, 3,3-dimethyl-1-butenyl, 3,3-dimethyl-2-butenyl, 1-ethyl-1-butenyl, 1-ethyl-2-butenyl, 1-ethyl-3-butenyl, 2-ethyl-1-butenyl, 2-ethyl-2-butenyl, 2-ethyl-3-butenyl, 1,1,2-trimethyl-2-propenyl, 1-ethyl-1-methyl-2-propenyl, 1-ethyl-2-methyl-1-propenyl and 1-ethyl-2-methyl-2-propenyl.

The term “alkynyl” also includes, in particular, straight-chain or branched open-chain hydrocarbon radicals having more than one triple bond, or else having one or more triple bonds and one or more double bonds, for example 1,3-butatrienyl or 3-penten-1-yn-1-yl. (C2-C6)-Alkynyl denotes, for example, ethynyl, 1-propynyl, 2-propynyl, 1-butynyl, 2-butynyl, 3-butynyl, 1-methyl-2-propynyl, 1-pentynyl, 2-pentynyl, 3-pentynyl, 4-pentynyl, 1-methyl-2-butynyl, 1-methyl-3-butynyl, 2-methyl-3-butynyl, 3-methyl-1-butynyl, 1,1-dimethyl-2-propynyl, 1-ethyl-2-propynyl, 1-hexynyl, 2-hexynyl, 3-hexynyl, 4-hexynyl, 5-hexynyl, 1-methyl-2-pentynyl, 1-methyl-3-pentynyl, 1-methyl-4-pentynyl, 2-methyl-3-pentynyl, 2-methyl-4-pentynyl, 3-methyl-1-pentynyl, 3-methyl-4-pentynyl, 4-methyl-1-pentynyl, 4-methyl-2-pentynyl, 1,1-dimethyl-2-butynyl, 1,1-dimethyl-3-butynyl, 1,2-dimethyl-3-butynyl, 2,2-dimethyl-3-butynyl, 3,3-dimethyl-1-butynyl, 1-ethyl-2-butynyl, 1-ethyl-3-butynyl, 2-ethyl-3-butynyl and 1-ethyl-1-methyl-2-propynyl.

The term “cycloalkyl” refers to a carbocyclic saturated ring system having preferably 3-8 ring carbon atoms, for example cyclopropyl, cyclobutyl, cyclopentyl or cyclohexyl, which optionally has further substitution, preferably by hydrogen, alkyl, alkoxy, cyano, nitro, alkylthio, haloalkylthio, halogen, alkenyl, alkynyl, haloalkyl, amino, alkylamino, bisalkylamino, alkoxycarbonyl, hydroxycarbonyl, arylalkoxycarbonyl, aminocarbonyl, alkylaminocarbonyl, cycloalkylaminocarbonyl. In the case of optionally substituted cycloalkyl, cyclic systems with substituents are included, also including substituents with a double bond on the cycloalkyl radical, for example an alkylidene group such as methylidene. In the case of optionally substituted cycloalkyl, polycyclic aliphatic systems are also included, for example bicyclo[1.1.0]butan-1-yl, bicyclo[1.1.0]butan-2-yl, bicyclo[2.1.0]pentan-1-yl, bicyclo[1.1.1]pentan-1-yl, bicyclo[2.1.0]pentan-2-yl, bicyclo[2.1.0]pentan-5-yl, bicyclo[2.1.1]hexyl, bicyclo[2.2.1]hept-2-yl, bicyclo[2.2.2]octan-2-yl, bicyclo[3.2.1]octan-2-yl, bicyclo[3.2.2]nonan-2-yl, adamantan-1-yl and adamantan-2-yl, but also systems such as 1,1′-bi(cyclopropyl)-1-yl, 1,1′-bi(cyclopropyl)-2-yl, for example. The term “(C3-C7)-cycloalkyl” is a brief notation for cycloalkyl having three to 7 carbon atoms, corresponding to the range specified for carbon atoms.

In the case of substituted cycloalkyl, spirocyclic aliphatic systems are also included, for example spiro[2.2]pent-1-yl, spiro[2.3]hex-1-yl, spiro[2.3]hex-4-yl, 3-spiro[2.3]hex-5-yl, spiro[3.3]hept-1-yl, spiro[3.3]hept-2-yl.

“Cycloalkenyl” denotes a carbocyclic, nonaromatic, partially unsaturated ring system having preferably 4-8 carbon atoms, e.g. 1-cyclobutenyl, 2-cyclobutenyl, 1-cyclopentenyl, 2-cyclopentenyl, 3-cyclopentenyl, or 1-cyclohexenyl, 2-cyclohexenyl, 3-cyclohexenyl, 1,3-cyclohexadienyl or 1,4-cyclohexadienyl, also including substituents with a double bond on the cycloalkenyl radical, for example an alkylidene group such as methylidene. In the case of optionally substituted cycloalkenyl, the elucidations for substituted cycloalkyl apply correspondingly.

The term “alkylidene”, also, for example, in the form (C1-C10)-alkylidene, means the radical of a straight-chain or branched open-chain hydrocarbon radical which is bonded via a double bond. Possible bonding sites for alkylidene are naturally only positions on the base structure where two hydrogen atoms can be replaced by the double bond; radicals are, for example, ═CH2, ═CH—CH3, ═C(CH3)—CH3, ═C(CH3)—C2H5 or ═C(C2H5)—C2H5. Cycloalkylidene denotes a carbocyclic radical bonded via a double bond.

“Arylalkyl” represents an aryl radical bonded via an alkyl group, “heteroarylalkyl” denotes a heteroaryl radical bonded via an alkyl group, and “heterocyclylalkyl” denotes a heterocyclyl radical bonded via an alkyl group.

According to the invention, “haloalkylthio”—on its own or as constituent part of a chemical group—represents straight-chain or branched S-haloalkyl, preferably having 1 to 8, or having 1 to 6 carbon atoms, such as (C1-C8)-, (C1-C6)- or (C1-C4)-haloalkylthio, for example (but not limited thereto) trifluoromethylthio, pentafluoroethylthio, difluoromethyl, 2,2-difluoroeth-1-ylthio, 2,2,2-difluoroeth-1-ylthio, 3,3,3-prop-1-ylthio.

“Halocycloalkyl” denotes cycloalkyl which is partially or fully substituted by identical or different halogen atoms, such as F, Cl and Br, or by haloalkyl, such as trifluoromethyl or difluoromethyl, for example 1-fluorocycloprop-1-yl, 2-fluorocycloprop-1-yl, 2,2-difluorocycloprop-1-yl, 1-fluorocyclobut-1-yl, 1-trifluoromethylcycloprop-1-yl, 2-trifluoromethylcycloprop-1-yl, 1-chlorocycloprop-1-yl, 2-chlorocycloprop-1-yl, 2,2-dichlorocycloprop-1-yl, 3,3-difluorocyclobutyl.

According to the invention, “trialkylsilyl”—on its own or as constituent part of a chemical group—represents straight-chain or branched Si-alkyl, preferably having 1 to 8, or having 1 to 6 carbon atoms, such as tri[(C1-C0—, (C1-C6)- or (C1-C4)-alkyl]silyl, for example (but not limited thereto) trimethylsilyl, triethylsilyl, tri(n-propyl)silyl, tri(isopropyl)silyl, tri(n-butyl)silyl, tri(1-methylprop-1-yl)silyl, tri(2-methylprop-1-yl)silyl, tri(1,1-dimethyleth-1-yl)silyl, tri(2,2-dimethyleth-1-yl)silyl.

If the compounds can form, through a hydrogen shift, tautomers whose structure is not formally covered by the general formula (I), these tautomers are nevertheless covered by the definition of the compounds of the general formula (I) according to the invention, unless a particular tautomer is under consideration. For example, many carbonyl compounds may be present both in the keto form and in the enol form, both forms being encompassed by the definition of the compound of the general formula (I).

Depending on the nature of the substituents and the manner in which they are attached, the compounds of the general formula (I) may be present as stereoisomers. The possible stereoisomers defined by the specific three-dimensional form thereof, such as enantiomers, diastereomers, Z and E isomers, are all encompassed by the general formula (I). If, for example, one or more alkenyl groups are present, diastereomers (Z and E isomers) may occur. If, for example, one or more asymmetric carbon atoms are present, enantiomers and diastereomers may occur. Stereoisomers can be obtained from the mixtures obtained in the preparation by customary separation methods. The chromatographic separation can be effected either on the analytical scale to find the enantiomeric excess or the diastereomeric excess, or else on the preparative scale to produce test specimens for biological testing. It is likewise possible to selectively prepare stereoisomers by using stereoselective reactions with use of optically active starting materials and/or auxiliaries. The invention thus also relates to all stereoisomers which are embraced by the general formula (I) but are not shown in their specific stereomeric form, and to mixtures thereof.

If the compounds are obtained as solids, the purification can also be carried out by recrystallization or digestion. If individual compounds (I) cannot be obtained in a satisfactory manner by the routes described below, they can be prepared by derivatization of other compounds (I).

Suitable isolation methods, purification methods and methods for separating stereoisomers of compounds of the general formula (I) are methods generally known to the person skilled in the art from analogous cases, for example by physical processes such as crystallization, chromatographic methods, in particular column chromatography and HPLC (high pressure liquid chromatography), distillation, optionally under reduced pressure, extraction and other methods; any mixtures that remain can generally be separated by chromatographic separation, for example on chiral solid phases. Suitable for preparative amounts or on an industrial scale are processes such as crystallization, for example of diastereomeric salts which can be obtained from the diastereomer mixtures using optically active acids and, if appropriate, provided that acidic groups are present, using optically active bases.

The present invention also claims processes for preparing the compounds of the general formula (I) according to the invention.

The compounds of the general formula (I) according to the invention can be prepared, inter alia, using known processes. The synthesis routes used and examined proceed from commercially available or easily preparable building blocks. In the schemes which follow, the moieties X, A, R1, R2, R3 and m of the general formula (I) have the meanings defined above, unless illustrative but non-limiting definitions are given.

Compounds according to the invention where A represents S(O)n can be prepared, for example, by the method shown in Scheme 1.

The pyridines of the general formula (Ia) can be prepared by coupling the pyridines (E-III), where LG represents a leaving group, with the disulfide (E-IV) in the presence of either zinc(0) and palladium catalysts (such as, for example, Pd(dppf)Cl2-CH2Cl2), or copper(0) and bases. The base may be an acetate salt of an alkali metal (for example sodium or potassium). The reactions are generally conducted in an organic solvent, for example tetrahydrofuran, dimethyl sulfoxide or dimethylformamide, at temperatures between 0° C. and the boiling point of the solvent.

The pyridines of the general formula (E-III) can be prepared by alkylation of the pyridines (E-I) in the presence of bases with the pyri(mi)dine (E-II), where LG represents a leaving group, and copper(I) salts. The base may be a carbonate salt of an alkali metal (for example sodium, potassium or cesium). The copper salts may be copper halides, for example copper(I) iodide. The reactions are generally carried out in an organic solvent, for example acetonitrile or dimethylformamide, at temperatures between 0° C. and the boiling point of the solvent.

Pyridines of the general formula (E-I) are known from the literature and can be prepared, for example, according to the methods described in Organic Letters (2016), 18, 3106-9, WO2013/14170 and similar methods.

Compounds according to the invention where n represents 1 or 2 can be prepared, for example, by the method shown in Scheme 2.

The sulfones and sulfoxides of the general formula (Ib) can be prepared by oxidation of the pyridines (Ia). Such reactions are known to the person skilled in the art and are described, for example, in Advanced Synthesis & Catalysis (2011), 351(2+3), 295-102.

The pyridines of the general formula (Ic) can be prepared by coupling of the pyridines (E-VII) with the alkyl halide (E-VIII), where Hal represents a halogen, in the presence of palladium catalysts (for example Pd(PPh3)4) and bases. The base may be a carbonate salt of an alkali metal (for example sodium or potassium). The reactions are generally conducted in an organic solvent, for example tetrahydrofuran, toluene or ethanol with or without addition of water, at temperatures between 0° C. and the boiling point of the solvent.

The pyridines of the general formula (E-VII) can be prepared by coupling of the pyridines (E-VI), where Hal represents a halogen, with pinacolborane or bis(pinacolato)diboron in the presence of palladium catalysts (for example Pd(MeCN)2Cl2), ligands (for example XPhos) and bases. The base may be an amine (for example triethylamine). The reactions are generally carried out in an organic solvent, for example tetrahydrofuran or dioxane, at temperatures between 0° C. and the boiling point of the solvent.

The pyridines of the general formula (E-VI) can be prepared by alkylation of the pyridines (E-V) in the presence of bases with the pyri(mi)dine (E-II), where LG represents a leaving group, and copper(I) salts. The base may be a carbonate salt of an alkali metal (for example sodium, potassium or cesium). The copper salts may be copper halides, for example copper(I) iodide. The reactions are generally carried out in an organic solvent, for example acetonitrile or dimethylformamide, at temperatures between 0° C. and the boiling point of the solvent.

Pyridines of the general formula (E-V) are known from the literature and can be prepared, for example, by the methods like those described in J. Am. Chem. Soc. (1952), 74, 1916-9.

The pyridines of the general formula (Id) can be prepared by alkylation of the pyridines (E-XII) in the presence of bases with the pyri(mi)dine (E-II), where LG represents a leaving group, and copper(I) salts. The base may be a carbonate salt of an alkali metal (for example sodium, potassium or cesium). The copper salts may be copper halides, for example copper(I) iodide. The reactions are generally carried out in an organic solvent, for example acetonitrile or dimethylformamide, at temperatures between 0° C. and the boiling point of the solvent.

The pyridines of the general formula (E-XII) can be prepared by demethylation of the pyridines (E-XI) in the presence of either hydrobromic acid and acetic acid or boron tribromide. The reactions with boron tribromide are generally carried out in an organic solvent, for example dichloromethane, at temperatures between 0° C. and the boiling point of the solvent.

The pyridines of the general formula (E-XI) can be prepared by coupling of the pyridines (E-IX) with the boronic acid (E-X) in the presence of copper(II) catalysts (for example Cu(OAc)2) and bases. The base may be an amine (for example triethylamine). The reactions are generally carried out in an organic solvent, for example dichloromethane, at temperatures between 0° C. and the boiling point of the solvent.

Pyridines of the general formula (E-IX) are known from the literature and can be prepared, for example, according to the methods described in EP1357111 and similar methods.

Selected detailed synthesis examples for the compounds of the general formula (I) according to the invention are given below. The 1H NMR, 13C-NMR and 19F-NMR spectroscopy data reported for the chemical examples described in the sections which follow (400 MHz for 1H NMR and 150 MHz for 13C-NMR and 375 MHz for 19F-NMR, solvent CDCl3, CD3OD or d6-DMSO, internal standard: tetramethylsilane 6=0.00 ppm) were obtained on a Bruker instrument, and the signals listed have the meanings given below: br=broad; s=singlet, d=doublet, t=triplet, dd=doublet of doublets, ddd=doublet of a doublet of doublets, m=multiplet, q=quartet, quint=quintet, sext=sextet, sept=septet, dq=doublet of quartets, dt=doublet of triplets. In the case of diastereomer mixtures, either the significant signals for each of the two diastereomers are reported or the characteristic signal of the main diastereomer is reported. The abbreviations used for chemical groups have, for example, the following meanings: Me=CH3, Et=CH2CH3, t-Hex=C(CH3)2CH(CH3)2, t-Bu=C(CH3)3, n-Bu=unbranched butyl, n-Pr=unbranched propyl, i-Pr=branched propyl, c-Pr=cyclopropyl, c-Hex=cyclohexyl.

SYNTHESIS EXAMPLES Table Example Number 1-216 Synthesis Step 1: 2-[(3-Bromo-4-methyl-2-pyridyl)oxy]pyrimidine

In a microwave, a mixture of 3-bromo-4-methylpyridin-2-ol (1.00 g, 5.32 mmol), 2-chloropyrimidine (609 mg, 5.32 mmol), copper(I) iodide (1.02 g, 5.36 mmol), cesium carbonate (3.50 g, 10.8 mmol) and DMF (15 ml) is heated under nitrogen at 150° C. for 1 h. The resulting reaction mixture is filtered and concentrated. The resulting crude product is dissolved in ethyl acetate and the solution is washed with sat. sodium chloride solution, dried over magnesium sulfate, filtered and concentrated. Final purification of the resulting crude product by column chromatography (ethyl acetate/heptane gradient) gives 2-[(3-bromo-4-methyl-2-pyridyl)oxy]pyrimidine (110 mg, 8% of theory).

Synthesis Step 2: 2-[(4-Methyl-3-phenylsulfanyl-2-pyridyl)oxy]pyrimidine (table example No. I-216)

Under nitrogen, a mixture of 2-[(3-bromo-4-methyl-2-pyridyl)oxy]pyrimidine (280 mg, 1.05 mmol), diphenyl disulfide (138 mg, 0.63 mmol), copper (100 mg, 1.58 mmol), potassium acetate (206 mg, 2.10 mmol) and dimethyl sulfoxide (6 ml) is heated at 100° C. for 40 h. The resulting reaction mixture is filtered and concentrated. By final purification by column chromatography (ethyl acetate/heptane gradient), 2-[(4-methyl-3-phenylsulfanyl-2-pyridyl)oxy]pyrimidine (74 mg, 24% of theory) is isolated.

Table Example Number 1-533 Synthesis Step 1: 2-Methoxy-6-methyl-3-phenoxypyridine

Under argon and at room temperature, a mixture of 2-methoxy-6-methylpyridin-3-ol (960 mg, 6.89 mmol), benzeneboronic acid (1.00 g, 8.27 mmol), copper(II) acetate (2.13 g, 11.7 mmol), triethylamine (1.92 ml, 13.7 mmol), 4 Å molecular sieves and dichloromethane (38 ml) is stirred for 72 h. The resulting reaction mixture is filtered and concentrated. By final purification by column chromatography (ethyl acetate/heptane gradient), 2-methoxy-6-methyl-3-phenoxypyridine (925 mg, 62% of theory) is isolated.

Synthesis Step 2: 6-Methyl-3-phenoxypyridin-2-ol

A mixture of 2-methoxy-6-methyl-3-phenoxypyridine (925 mg, 4.29 mmol), hydrobromic acid (45% strength solution in acetic acid, 5.2 ml, 42.9 mmol) and acetic acid (20 ml) is heated at 100° C. for 1 h. The resulting reaction mixture is concentrated. The crude product is dissolved in water, adjusted to pH 5 with 2M NaOH and extracted with ethyl acetate. The combined organic phases are washed with sat. sodium chloride solution, dried over magnesium sulfate, filtered and concentrated. This gives 6-methyl-3-phenoxypyridin-2-ol (680 mg, 78% of theory).

Synthesis Step 3: 2-[(6-Methyl-3-phenoxy-2-pyridyl)oxy]-5-(trifluoromethyl)pyrimidine (Table Example No. I-533)

A mixture of 6-methyl-3-phenoxypyridin-2-ol (150 mg, 0.74 mmol), 2-chloro-5-trifluoromethylpyrimidine (280 mg, 1.52 mmol), copper(I) iodide (28 mg, 0.14 mmol), cesium carbonate (485 mg, 1.49 mmol) and acetonitrile (4 ml) is heated at 100° C. for 3 h. The resulting reaction mixture is filtered and concentrated. By final purification by column chromatography (ethyl acetate/heptane gradient), 2-[(6-methyl-3-phenoxy-2-pyridyl)oxy]-5-(trifluoromethyl)pyrimidine (153 mg, 59% of theory) is isolated.

Table Example Number 1-478 Synthesis Step 1: 2-[(3-Bromo-4,6-dimethyl-2-pyridyl)oxy]-5-fluoropyrimidine

A mixture of 3-bromo-4,6-dimethylpyridin-2-ol (3.35 g, 16.5 mmol), 2-chloro-5-fluoropyrimidine (3.29 g, 24.8 mmol), copper(I) iodide (630 mg, 3.31 mmol), cesium carbonate (10.8 g, 33.1 mmol) and dimethylformamide (15 ml) is heated at 130° C. for 18 h. The resulting reaction mixture is filtered and concentrated. By final purification by column chromatography (ethyl acetate/heptane gradient), 2-[(3-bromo-4,6-dimethyl-2-pyridyl)oxy]-5-fluoropyrimidine (1.58 g, 32% of theory) is isolated.

Synthesis Step 2: 2-[[4,6-Dimethyl-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-2-pyridyl]oxy]-5-fluoropyrimidine

Under argon, a mixture of 2-[(3-bromo-4,6-dimethyl-2-pyridyl)oxy]-5-fluoropyrimidine (1.54 g, 5.15 mmol), pinacolborane (920 mg, 7.21 mmol), triethylamine (4.1 ml, 29.3 mmol), Pd(MeCN)2Cl2 (54 mg, 0.20 mmol), X-Phos (197 mg, 0.41 mmol) and dioxane (25 ml) is heated at 110° C. for 8 h. The resulting reaction mixture is filtered and concentrated. By final purification by column chromatography (ethyl acetate/heptane gradient), 2-[[4,6-dimethyl-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-2-pyridyl]oxy]-5-fluoropyrimidine (1.58 g, 89% of theory) is isolated.

Synthesis Step 3: 2-[(3-Benzyl-4,6-dimethyl-2-pyridyl)oxy]-5-fluoropyrimidine (Table Example No. I-478)

Under argon, a mixture of 2-[[4,6-dimethyl-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-2-pyridyl]oxy]-5-fluoropyrimidine (140 mg, 0.40 mmol), benzyl bromide (105 mg, 0.60 mmol), sodium carbonate (86 mg, 0.81 mmol), Pd(PPh3)4 (47 mg, 0.04 mmol), toluene (1.3 ml), ethanol (0.3 ml) and water (0.3 ml) is heated at 80° C. for 1.5 hours. The resulting reaction mixture is filtered and concentrated. By final purification by column chromatography (ethyl acetate/heptane gradient), 2-[(3-benzyl-4,6-dimethyl-2-pyridyl)oxy]-5-fluoropyrimidine (98 mg, 78% of theory) is isolated.

In analogy to the preparation examples cited above and recited at the appropriate point, the compounds of the general formula (I) specified hereinafter and shown in Table 1 are obtained.

TABLE 1 Example number R2a R2b R3 X AR1 1-1 H H Cl CH 4-fluorophenoxy 1-2 H H Cl CH 3,4-difluorophenoxy 1-3 H H Cl CH 2,4-difluorophenoxy 1-4 H H Cl CH 3-(trifluoromethyl)phenoxy 1-5 H H Cl CH 3-chlorophenoxy 1-6 H H Cl CH 3-methoxyphenoxy 1-7 H H Cl CH 4-cyanophenoxy 1-8 H H Cl CH 4-methylphenoxy 1-9 H H Cl CH phenoxy 1-10 H H F CH 4-fluorophenoxy 1-11 H H F CH 3,4-difluorophenoxy 1-12 H H F CH 2,4-difluorophenoxy 1-13 H H F CH 3-(trifluoromethyl)phenoxy 1-14 H H F CH 3-chlorophenoxy 1-15 H H F CH 3-methoxyphenoxy 1-16 H H F CH 4-cyanophenoxy 1-17 H H F CH 4-methylphenoxy 1-18 H H F CH phenoxy 1-19 H H CF3 CH 4-fluorophenoxy 1-20 H H CF3 CH 3,4-difluorophenoxy 1-21 H H CF3 CH 2,4-difluorophenoxy 1-22 H H CF3 CH 3-(trifluoromethyl)phenoxy 1-23 H H CF3 CH 3-chlorophenoxy 1-24 H H CF3 CH 3-methoxyphenoxy 1-25 H H CF3 CH 4-cyanophenoxy 1-26 H H CF3 CH 4-methylphenoxy 1-27 H H CF3 CH phenoxy 1-28 H H H CH 4-fluorophenoxy 1-29 H H H CH 3,4-difluorophenoxy 1-30 H H H CH 2,4-difluorophenoxy 1-31 H H H CH 3-(trifluoromethyl)phenoxy 1-32 H H H CH 3-chlorophenoxy 1-33 H H H CH 3-methoxyphenoxy 1-34 H H H CH 4-cyanophenoxy 1-35 H H H CH 4-methylphenoxy 1-36 H H H CH phenoxy 1-37 H H Cl N 4-fluorophenoxy 1-38 H H Cl N 3,4-difluorophenoxy 1-39 H H Cl N 2,4-difluorophenoxy 1-40 H H Cl N 3-(trifluoromethyl)phenoxy 1-41 H H Cl N 3-chlorophenoxy 1-42 H H Cl N 3-methoxyphenoxy 1-43 H H Cl N 4-cyanophenoxy 1-44 H H Cl N 4-methylphenoxy 1-45 H H Cl N phenoxy 1-46 H H F N 4-fluorophenoxy 1-47 H H F N 3,4-difluorophenoxy 1-48 H H F N 2,4-difluorophenoxy 1-49 H H F N 3-(trifluoromethyl)phenoxy 1-50 H H F N 3-chlorophenoxy 1-51 H H F N 3-methoxyphenoxy 1-52 H H F N 4-cyanophenoxy 1-53 H H F N 4-methylphenoxy 1-54 H H F N phenoxy 1-55 H H CF3 N 4-fluorophenoxy 1-56 H H CF3 N 3,4-difluorophenoxy 1-57 H H CF3 N 2,4-difluorophenoxy 1-58 H H CF3 N 3-(trifluoromethyl)phenoxy 1-59 H H CF3 N 3-chlorophenoxy 1-60 H H CF3 N 3-methoxyphenoxy 1-61 H H CF3 N 4-cyanophenoxy 1-62 H H CF3 N 4-methylphenoxy 1-63 H H CF3 N phenoxy 1-64 H H H N 4-fluorophenoxy 1-65 H H H N 3,4-difluorophenoxy 1-66 H H H N 2,4-difluorophenoxy 1-67 H H H N 3-(trifluoromethyl)phenoxy 1-68 H H H N 3-chlorophenoxy 1-69 H H H N 3-methoxyphenoxy 1-70 H H H N 4-cyanophenoxy 1-71 H H H N 4-methylphenoxy 1-72 H H H N phenoxy 1-73 CH3 H Cl N 4-fluorophenoxy 1-74 CH3 H Cl N 3,4-difluorophenoxy 1-75 CH3 H Cl N 2,4-difluorophenoxy 1-76 CH3 H Cl N 3-(trifluoromethyl)phenoxy 1-77 CH3 H Cl N 3-chlorophenoxy 1-78 CH3 H Cl N 3-methoxyphenoxy 1-79 CH3 H Cl N 4-cyanophenoxy 1-80 CH3 H Cl N 4-methylphenoxy 1-81 CH3 H Cl N phenoxy 1-82 CH3 H F N 4-fluorophenoxy 1-83 CH3 H F N 3,4-difluorophenoxy 1-84 CH3 H F N 2,4-difluorophenoxy 1-85 CH3 H F N 3-(trifluoromethyl)phenoxy 1-86 CH3 H F N 3-chlorophenoxy 1-87 CH3 H F N 3-methoxyphenoxy 1-88 CH3 H F N 4-cyanophenoxy 1-89 CH3 H F N 4-methylphenoxy 1-90 CH3 H F N phenoxy 1-91 CH3 H CF3 N 4-fluorophenoxy 1-92 CH3 H CF3 N 3,4-difluorophenoxy 1-93 CH3 H CF3 N 2,4-difluorophenoxy 1-94 CH3 H CF3 N 3-(trifluoromethyl)phenoxy 1-95 CH3 H CF3 N 3-chlorophenoxy 1-96 CH3 H CF3 N 3-methoxyphenoxy 1-97 CH3 H CF3 N 4-cyanophenoxy 1-98 CH3 H CF3 N 4-methylphenoxy 1-99 CH3 H CF3 N phenoxy 1-100 CH3 H H N 4-fluorophenoxy 1-101 CH3 H H N 3,4-difluorophenoxy 1-102 CH3 H H N 2,4-difluorophenoxy 1-103 CH3 H H N 3-(trifluoromethyl)phenoxy 1-104 CH3 H H N 3-chlorophenoxy 1-105 CH3 H H N 3-methoxyphenoxy 1-106 CH3 H H N 4-cyanophenoxy 1-107 CH3 H H N 4-methylphenoxy 1-108 CH3 H H N phenoxy 1-109 H H Cl CH 4-fluorophenylthio 1-110 H H Cl CH 3,4-difluorophenylthio 1-111 H H Cl CH 2,4-difluorophenylthio 1-112 H H Cl CH 3-(trifluoromethyl)phenylthio 1-113 H H Cl CH 3-chlorophenylthio 1-114 H H Cl CH 3-methoxyphenylthio 1-115 H H Cl CH 4-cyanophenylthio 1-116 H H Cl CH 4-methylphenylthio 1-117 H H Cl CH phenylthio 1-118 H H F CH 4-fluorophenylthio 1-119 H H F CH 3,4-difluorophenylthio 1-120 H H F CH 2,4-difluorophenylthio 1-121 H H F CH 3-(trifluoromethyl)phenylthio 1-122 H H F CH 3-chlorophenylthio 1-123 H H F CH 3-methoxyphenylthio 1-124 H H F CH 4-cyanophenylthio 1-125 H H F CH 4-methylphenylthio 1-126 H H F CH phenylthio 1-127 H H CF3 CH 4-fluorophenylthio 1-128 H H CF3 CH 3,4-difluorophenylthio 1-129 H H CF3 CH 2,4-difluorophenylthio 1-130 H H CF3 CH 3-(trifluoromethyl)phenylthio 1-131 H H CF3 CH 3-chlorophenylthio 1-132 H H CF3 CH 3-methoxyphenylthio 1-133 H H CF3 CH 4-cyanophenylthio 1-134 H H CF3 CH 4-methylphenylthio 1-135 H H CF3 CH phenylthio 1-136 H H H CH 4-fluorophenylthio 1-137 H H H CH 3,4-difluorophenylthio 1-138 H H H CH 2,4-difluorophenylthio 1-139 H H H CH 3-(trifluoromethyl)phenylthio 1-140 H H H CH 3-chlorophenylthio 1-141 H H H CH 3-methoxyphenylthio 1-142 H H H CH 4-cyanophenylthio 1-143 H H H CH 4-methylphenylthio 1-144 H H H CH phenylthio 1-145 H H Cl N 4-fluorophenylthio 1-146 H H Cl N 3,4-difluorophenylthio 1-147 H H Cl N 2,4-difluorophenylthio 1-148 H H Cl N 3-(trifluoromethyl)phenylthio 1-149 H H Cl N 3-chlorophenylthio 1-150 H H Cl N 3-methoxyphenylthio 1-151 H H Cl N 4-cyanophenylthio 1-152 H H Cl N 4-methylphenylthio 1-153 H H Cl N phenylthio 1-154 H H F N 4-fluorophenylthio 1-155 H H F N 3,4-difluorophenylthio 1-156 H H F N 2,4-difluorophenylthio 1-157 H H F N 3-(trifluoromethyl)phenylthio 1-158 H H F N 3-chlorophenylthio 1-159 H H F N 3-methoxyphenylthio 1-160 H H F N 4-cyanophenylthio 1-161 H H F N 4-methylphenylthio 1-162 H H F N phenylthio 1-163 H H CF3 N 4-fluorophenylthio 1-164 H H CF3 N 3,4-difluorophenylthio 1-165 H H CF3 N 2,4-difluorophenylthio 1-166 H H CF3 N 3-(trifluoromethyl)phenylthio 1-167 H H CF3 N 3-chlorophenylthio 1-168 H H CF3 N 3-methoxyphenylthio 1-169 H H CF3 N 4-cyanophenylthio 1-170 H H CF3 N 4-methylphenylthio 1-171 H H CF3 N phenylthio 1-172 H H H N 4-fluorophenylthio 1-173 H H H N 3,4-difluorophenylthio 1-174 H H H N 2,4-difluorophenylthio 1-175 H H H N 3-(trifluoromethyl)phenylthio 1-176 H H H N 3-chlorophenylthio 1-177 H H H N 3-methoxyphenylthio 1-178 H H H N 4-cyanophenylthio 1-179 H H H N 4-methylphenylthio 1-180 H H H N phenylthio 1-181 CH3 H Cl N 4-fluorophenylthio 1-182 CH3 H Cl N 3,4-difluorophenylthio 1-183 CH3 H Cl N 2,4-difluorophenylthio 1-184 CH3 H Cl N 3-(trifluoromethyl)phenylthio 1-185 CH3 H Cl N 3-chlorophenylthio 1-186 CH3 H Cl N 3-methoxyphenylthio 1-187 CH3 H Cl N 4-cyanophenylthio 1-188 CH3 H Cl N 4-methylphenylthio 1-189 CH3 H Cl N phenylthio 1-190 CH3 H F N 4-fluorophenylthio 1-191 CH3 H F N 3,4-difluorophenylthio 1-192 CH3 H F N 2,4-difluorophenylthio 1-193 CH3 H F N 3-(trifluoromethyl)phenylthio 1-194 CH3 H F N 3-chlorophenylthio 1-195 CH3 H F N 3-methoxyphenylthio 1-196 CH3 H F N 4-cyanophenylthio 1-197 CH3 H F N 4-methylphenylthio 1-198 CH3 H F N phenylthio 1-199 CH3 H CF3 N 4-fluorophenylthio 1-200 CH3 H CF3 N 3,4-difluorophenylthio 1-201 CH3 H CF3 N 2,4-difluorophenylthio 1-202 CH3 H CF3 N 3-(trifluoromethyl)phenylthio 1-203 CH3 H CF3 N 3-chlorophenylthio 1-204 CH3 H CF3 N 3-methoxyphenylthio 1-205 CH3 H CF3 N 4-cyanophenylthio 1-206 CH3 H CF3 N 4-methylphenylthio 1-207 CH3 H CF3 N phenylthio 1-208 CH3 H H N 4-fluorophenylthio 1-209 CH3 H H N 3,4-difluorophenylthio 1-210 CH3 H H N 2,4-difluorophenylthio 1-211 CH3 H H N 3-(trifluoromethyl)phenylthio 1-212 CH3 H H N 3-chlorophenylthio 1-213 CH3 H H N 3-methoxyphenylthio 1-214 CH3 H H N 4-cyanophenylthio 1-215 CH3 H H N 4-methylphenylthio 1-216 CH3 H H N phenylthio 1-217 H H Cl CH 4-fluorophenylmethyl 1-218 H H Cl CH 3,4-difluorophenylmethyl 1-219 H H Cl CH 2,4-difluorophenylmethyl 1-220 H H Cl CH 3-(trifluoromethyl)phenylmethyl 1-221 H H Cl CH 3-chlorophenylmethyl 1-222 H H Cl CH 3-methoxyphenylmethyl 1-223 H H Cl CH 4-cyanophenylmethyl 1-224 H H Cl CH 4-methylphenylmethyl 1-225 H H Cl CH benzyl 1-226 H H F CH 4-fluorophenylmethyl 1-227 H H F CH 3,4-difluorophenylmethyl 1-228 H H F CH 2,4-difluorophenylmethyl 1-229 H H F CH 3-(trifluoromethyl)phenylmethyl 1-230 H H F CH 3-chlorophenylmethyl 1-231 H H F CH 3-methoxyphenylmethyl 1-232 H H F CH 4-cyanophenylmethyl 1-233 H H F CH 4-methylphenylmethyl 1-234 H H F CH benzyl 1-235 H H CF3 CH 4-fluorophenylmethyl 1-236 H H CF3 CH 3,4-difluorophenylmethyl 1-237 H H CF3 CH 2,4-difluorophenylmethyl 1-238 H H CF3 CH 3-(trifluoromethyl)phenylmethyl 1-239 H H CF3 CH 3-chlorophenylmethyl 1-240 H H CF3 CH 3-methoxyphenylmethyl 1-241 H H CF3 CH 4-cyanophenylmethyl 1-242 H H CF3 CH 4-methylphenylmethyl 1-243 H H CF3 CH benzyl 1-244 H H H CH 4-fluorophenylmethyl 1-245 H H H CH 3,4-difluorophenylmethyl 1-246 H H H CH 2,4-difluorophenylmethyl 1-247 H H H CH 3-(trifluoromethyl)phenylmethyl 1-248 H H H CH 3-chlorophenylmethyl 1-249 H H H CH 3-methoxyphenylmethyl 1-250 H H H CH 4-cyanophenylmethyl 1-251 H H H CH 4-methylphenylmethyl 1-252 H H H CH benzyl 1-253 H H Cl N 4-fluorophenylmethyl 1-254 H H Cl N 3,4-difluorophenylmethyl 1-255 H H Cl N 2,4-difluorophenylmethyl 1-256 H H Cl N 3-(trifluoromethyl)phenylmethyl 1-257 H H Cl N 3-chlorophenylmethyl 1-258 H H Cl N 3-methoxyphenylmethyl 1-259 H H Cl N 4-cyanophenylmethyl 1-260 H H Cl N 4-methylphenylmethyl 1-261 H H Cl N benzyl 1-262 H H F N 4-fluorophenylmethyl 1-263 H H F N 3,4-difluorophenylmethyl 1-264 H H F N 2,4-difluorophenylmethyl 1-265 H H F N 3-(trifluoromethyl)phenylmethyl 1-266 H H F N 3-chlorophenylmethyl 1-267 H H F N 3-methoxyphenylmethyl 1-268 H H F N 4-cyanophenylmethyl 1-269 H H F N 4-methylphenylmethyl 1-270 H H F N benzyl 1-271 H H CF3 N 4-fluorophenylmethyl 1-272 H H CF3 N 3,4-difluorophenylmethyl 1-273 H H CF3 N 2,4-difluorophenylmethyl 1-274 H H CF3 N 3-(trifluoromethyl)phenylmethyl 1-275 H H CF3 N 3-chlorophenylmethyl 1-276 H H CF3 N 3-methoxyphenylmethyl 1-277 H H CF3 N 4-cyanophenylmethyl 1-278 H H CF3 N 4-methylphenylmethyl 1-279 H H CF3 N benzyl 1-280 H H H N 4-fluorophenylmethyl 1-281 H H H N 3,4-difluorophenylmethyl 1-282 H H H N 2,4-difluorophenylmethyl 1-283 H H H N 3-(trifluoromethyl)phenylmethyl 1-284 H H H N 3-chlorophenylmethyl 1-285 H H H N 3-methoxyphenylmethyl 1-286 H H H N 4-cyanophenylmethyl 1-287 H H H N 4-methylphenylmethyl 1-288 H H H N benzyl 1-289 CH3 H Cl N 4-fluorophenylmethyl 1-290 CH3 H Cl N 3,4-difluorophenylmethyl 1-291 CH3 H Cl N 2,4-difluorophenylmethyl 1-292 CH3 H Cl N 3-(trifluoromethyl)phenylmethyl 1-293 CH3 H Cl N 3-chlorophenylmethyl 1-294 CH3 H Cl N 3-methoxyphenylmethyl 1-295 CH3 H Cl N 4-cyanophenylmethyl 1-296 CH3 H Cl N 4-methylphenylmethyl 1-297 CH3 H Cl N benzyl 1-298 CH3 H F N 4-fluorophenylmethyl 1-299 CH3 H F N 3,4-difluorophenylmethyl 1-300 CH3 H F N 2,4-difluorophenylmethyl 1-301 CH3 H F N 3-(trifluoromethyl)phenylmethyl 1-302 CH3 H F N 3-chlorophenylmethyl 1-303 CH3 H F N 3-methoxyphenylmethyl 1-304 CH3 H F N 4-cyanophenylmethyl 1-305 CH3 H F N 4-methylphenylmethyl 1-306 CH3 H F N benzyl 1-307 CH3 H CF3 N 4-fluorophenylmethyl 1-308 CH3 H CF3 N 3,4-difluorophenylmethyl 1-309 CH3 H CF3 N 2,4-difluorophenylmethyl 1-310 CH3 H CF3 N 3-(trifluoromethyl)phenylmethyl 1-311 CH3 H CF3 N 3-chlorophenylmethyl 1-312 CH3 H CF3 N 3-methoxyphenylmethyl 1-313 CH3 H CF3 N 4-cyanophenylmethyl 1-314 CH3 H CF3 N 4-methylphenylmethyl 1-315 CH3 H CF3 N benzyl 1-316 CH3 H H N 4-fluorophenylmethyl 1-317 CH3 H H N 3,4-difluorophenylmethyl 1-318 CH3 H H N 2,4-difluorophenylmethyl 1-319 CH3 H H N 3-(trifluoromethyl)phenylmethyl 1-320 CH3 H H N 3-chlorophenylmethyl 1-321 CH3 H H N 3-methoxyphenylmethyl 1-322 CH3 H H N 4-cyanophenylmethyl 1-323 CH3 H H N 4-methylphenylmethyl 1-324 CH3 H H N benzyl 1-325 H H Cl N 4-fluorophenylamino 1-326 H H Cl N 3,4-difluorophenylamino 1-327 H H Cl N 2,4-difluorophenylamino 1-328 H H Cl N 3-(trifluoromethyl)phenylamino 1-329 H H Cl N 3-chlorophenylamino 1-330 H H Cl N 3-methoxyphenylamino 1-331 H H Cl N 4-cyanophenylamino 1-332 H H Cl N 4-methylphenylamino 1-333 H H Cl N phenylamino 1-334 H H F N 4-fluorophenylamino 1-335 H H F N 3,4-difluorophenylamino 1-336 H H F N 2,4-difluorophenylamino 1-337 H H F N 3-(trifluoromethyl)phenylamino 1-338 H H F N 3-chlorophenylamino 1-339 H H F N 3-methoxyphenylamino 1-340 H H F N 4-cyanophenylamino 1-341 H H F N 4-methylphenylamino 1-342 H H F N phenylamino 1-343 H H CF3 N 4-fluorophenylamino 1-344 H H CF3 N 3,4-difluorophenylamino 1-345 H H CF3 N 2,4-difluorophenylamino 1-346 H H CF3 N 3-(trifluoromethyl)phenylamino 1-347 H H CF3 N 3-chlorophenylamino 1-348 H H CF3 N 3-methoxyphenylamino 1-349 H H CF3 N 4-cyanophenylamino 1-350 H H CF3 N 4-methylphenylamino 1-351 H H CF3 N phenylamino 1-352 H H H N 4-fluorophenylamino 1-353 H H H N 3,4-difluorophenylamino 1-354 H H H N 2,4-difluorophenylamino 1-355 H H H N 3-(trifluoromethyl)phenylamino 1-356 H H H N 3-chlorophenylamino 1-357 H H H N 3-methoxyphenylamino 1-358 H H H N 4-cyanophenylamino 1-359 H H H N 4-methylphenylamino 1-360 H H H N phenylamino 1-361 CH3 H Cl N 4-fluorophenylamino 1-362 CH3 H Cl N 3,4-difluorophenylamino 1-363 CH3 H Cl N 2,4-difluorophenylamino 1-364 CH3 H Cl N 3-(trifluoromethyl)phenylamino 1-365 CH3 H Cl N 3-chlorophenylamino 1-366 CH3 H Cl N 3-methoxyphenylamino 1-367 CH3 H Cl N 4-cyanophenylamino 1-368 CH3 H Cl N 4-methylphenylamino 1-369 CH3 H Cl N phenylamino 1-370 CH3 H F N 4-fluorophenylamino 1-371 CH3 H F N 3,4-difluorophenylamino 1-372 CH3 H F N 2,4-difluorophenylamino 1-373 CH3 H F N 3-(trifluoromethyl)phenylamino 1-374 CH3 H F N 3-chlorophenylamino 1-375 CH3 H F N 3-methoxyphenylamino 1-376 CH3 H F N 4-cyanophenylamino 1-377 CH3 H F N 4-methylphenylamino 1-378 CH3 H F N phenylamino 1-379 CH3 H CF3 N 4-fluorophenylamino 1-380 CH3 H CF3 N 3,4-difluorophenylamino 1-381 CH3 H CF3 N 2,4-difluorophenylamino 1-382 CH3 H CF3 N 3-(trifluoromethyl)phenylamino 1-383 CH3 H CF3 N 3-chlorophenylamino 1-384 CH3 H CF3 N 3-methoxyphenylamino 1-385 CH3 H CF3 N 4-cyanophenylamino 1-386 CH3 H CF3 N 4-methylphenylamino 1-387 CH3 H CF3 N phenylamino 1-388 CH3 H H N 4-fluorophenylamino 1-389 CH3 H H N 3,4-difluorophenylamino 1-390 CH3 H H N 2,4-difluorophenylamino 1-391 CH3 H H N 3-(trifluoromethyl)phenylamino 1-392 CH3 H H N 3-chlorophenylamino 1-393 CH3 H H N 3-methoxyphenylamino 1-394 CH3 H H N 4-cyanophenylamino 1-395 CH3 H H N 4-methylphenylamino 1-396 CH3 H H N phenylamino 1-397 H CH3 Cl N benzyl 1-398 H CH3 Cl N 4-fluorophenylmethyl 1-399 H CH3 Cl N 3,4-difluorophenylmethyl 1-400 H CH3 Cl N 2,4-difluorophenylmethyl 1-401 H CH3 Cl N 4-chlorophenylmethyl 1-402 H CH3 Cl N (3-fluoro-4-methylphenyl)methyl 1-403 H CH3 Cl N 3-methoxyphenylmethyl 1-404 H CH3 Cl N (3-fluoro-4-chlorophenyl)methyl 1-405 H CH3 Cl N 4-methylphenylmethyl 1-406 H CH3 Cl N (4-fluoro-3- methoxyphenyl)methyl 1-407 H CH3 Cl N (2,4-difluoro-3- methoxyphenyl)methyl 1-408 H CH3 Cl CH benzyl 1-409 H CH3 Cl CH 4-fluorophenylmethyl 1-410 H CH3 Cl CH 3,4-difluorophenylmethyl 1-411 H CH3 Cl CH 2,4-difluorophenylmethyl 1-412 H CH3 Cl CH 4-chlorophenylmethyl 1-413 H CH3 Cl CH (3-fluoro-4-methylphenyl)methyl 1-414 H CH3 Cl CH 3-methoxyphenylmethyl 1-415 H CH3 Cl CH (3-fluoro-4-chlorophenyl)methyl 1-416 H CH3 Cl CH 4-methylphenylmethyl 1-417 H CH3 Cl CH (4-fluoro-3- methoxyphenyl)methyl 1-418 H CH3 Cl CH (2,4-difluoro-3- methoxyphenyl)methyl 1-419 H CH3 Cl CF benzyl 1-420 H CH3 Cl CF 4-fluorophenylmethyl 1-421 H CH3 Cl CF 3,4-difluorophenylmethyl 1-422 H CH3 Cl CF 2,4-difluorophenylmethyl 1-423 H CH3 Cl CF 4-chlorophenylmethyl 1-424 H CH3 Cl CF (3-fluoro-4-methylphenyl)methyl 1-425 H CH3 Cl CF 3-methoxyphenylmethyl 1-426 H CH3 Cl CF (3-fluoro-4-chlorophenyl)methyl 1-427 H CH3 Cl CF 4-methylphenylmethyl 1-428 H CH3 Cl CF (4-fluoro-3- methoxyphenyl)methyl 1-429 H CH3 Cl CF (2,4-difluoro-3- methoxyphenyl)methyl 1-430 H CH3 F N benzyl 1-431 H CH3 F N 4-fluorophenylmethyl 1-432 H CH3 F N 3,4-difluorophenylmethyl 1-433 H CH3 F N 2,4-difluorophenylmethyl 1-434 H CH3 F N 4-chlorophenylmethyl 1-435 H CH3 F N (3-fluoro-4-methylphenyl)methyl 1-436 H CH3 F N 3-methoxyphenylmethyl 1-437 H CH3 F N (3-fluoro-4-chlorophenyl)methyl 1-438 H CH3 F N 4-methylphenylmethyl 1-439 H CH3 F N (4-fluoro-3- methoxyphenyl)methyl 1-440 H CH3 F N (2,4-difluoro-3- methoxyphenyl)methyl 1-441 H CH3 H N benzyl 1-442 H CH3 H N 4-fluorophenylmethyl 1-443 H CH3 H N 3,4-difluorophenylmethyl 1-444 H CH3 H N 2,4-difluorophenylmethyl 1-445 H CH3 H N 4-chlorophenylmethyl 1-446 H CH3 H N (3-fluoro-4-methylphenyl)methyl 1-447 H CH3 H N 3-methoxyphenylmethyl 1-448 H CH3 H N (3-fluoro-4-chlorophenyl)methyl 1-449 H CH3 H N 4-methylphenylmethyl 1-450 H CH3 H N (4-fluoro-3- methoxyphenyl)methyl 1-451 H CH3 H N (2,4-difluoro-3- methoxyphenyl)methyl 1-452 H CH3 H CH benzyl 1-453 H CH3 H CH 4-fluorophenylmethyl 1-454 H CH3 H CH 3,4-difluorophenylmethyl 1-455 H CH3 H CH 2,4-difluorophenylmethyl 1-456 H CH3 H CH 4-chlorophenylmethyl 1-457 H CH3 H CH (3-fluoro-4-methylphenyl)methyl 1-458 H CH3 H CH 3-methoxyphenylmethyl 1-459 H CH3 H CH (3-fluoro-4-chlorophenyl)methyl 1-460 H CH3 H CH 4-methylphenylmethyl 1-461 H CH3 H CH (4-fluoro-3- methoxyphenyl)methyl 1-462 H CH3 H CH (2,4-difluoro,3- methoxyphenyl)methyl 1-463 H CH3 CF3 N benzyl 1-464 H CH3 CF3 N 2,4-difluorophenylmethyl 1-465 H CH3 CF3 N (4-fluoro-3- methoxyphenyl)methyl 1-466 H CH3 CF3 N 4-methylphenylmethyl 1-467 CH3 CH3 Cl N benzyl 1-468 CH3 CH3 Cl N 4-fluorophenylmethyl 1-469 CH3 CH3 Cl N 3,4-difluorophenylmethyl 1-470 CH3 CH3 Cl N 2,4-difluorophenylmethyl 1-471 CH3 CH3 Cl N 4-chlorophenylmethyl 1-472 CH3 CH3 Cl N (3-fluoro-4-methylphenyl)methyl 1-473 CH3 CH3 Cl N 3-methoxyphenylmethyl 1-474 CH3 CH3 Cl N (3-fluoro-4-chlorophenyl)methyl 1-475 CH3 CH3 Cl N 4-methylphenylmethyl 1-476 CH3 CH3 Cl N (4-fluoro-3- methoxyphenyl)methyl 1-477 CH3 CH3 Cl N (2,4-difluoro-3- methoxyphenyl)methyl 1-478 CH3 CH3 F N benzyl 1-479 CH3 CH3 F N 4-fluorophenylmethyl 1-480 CH3 CH3 F N 3,4-difluorophenylmethyl 1-481 CH3 CH3 F N 2,4-difluorophenylmethyl 1-482 CH3 CH3 F N 4-chlorophenylmethyl 1-483 CH3 CH3 F N (3-fluoro-4-methylphenyl)methyl 1-484 CH3 CH3 F N 3-methoxyphenylmethyl 1-485 CH3 CH3 F N (3-fluoro-4-chlorophenyl)methyl 1-486 CH3 CH3 F N 4-methylphenylmethyl 1-487 CH3 CH3 F N (4-fluoro-3- methoxyphenyl)methyl 1-488 CH3 CH3 F N (2,4-difluoro-3- methoxyphenyl)methyl 1-489 CH3 CH3 H N benzyl 1-490 CH3 CH3 H N 4-fluorophenylmethyl 1-491 CH3 CH3 H N 3,4-difluorophenylmethyl 1-492 CH3 CH3 H N 2,4-difluorophenylmethyl 1-493 CH3 CH3 H N 4-chlorophenylmethyl 1-494 CH3 CH3 H N (3-fluoro-4-methylphenyl)methyl 1-495 CH3 CH3 H N 3-methoxyphenylmethyl 1-496 CH3 CH3 H N (3-fluoro-4-chlorophenyl)methyl 1-497 CH3 CH3 H N 4-methylphenylmethyl 1-498 CH3 CH3 H N (4-fluoro-3- methoxyphenyl)methyl 1-499 CH3 CH3 H N (2,4-difluoro-3- methoxyphenyl)methyl 1-500 H CH3 Cl N phenoxy 1-501 H CH3 Cl N 4-fluorophenoxy 1-502 H CH3 Cl N 3,4-difluorophenoxy 1-503 H CH3 Cl N 2,4-difluorophenoxy 1-504 H CH3 Cl N 4-chlorophenoxy 1-505 H CH3 Cl N 3-fluoro-4-methylphenoxy 1-506 H CH3 Cl N 3-methoxyphenoxy 1-507 H CH3 Cl N 3-fluoro-4-chlorophenoxy 1-508 H CH3 Cl N 4-methylphenoxy 1-509 H CH3 Cl N 4-fluoro-3-methoxyphenoxy 1-510 H CH3 Cl N 2,4-difluoro-3-methoxyphenoxy 1-511 H CH3 F N phenoxy 1-512 H CH3 F N 4-fluorophenoxy 1-513 H CH3 F N 3,4-difluorophenoxy 1-514 H CH3 F N 2,4-difluorophenoxy 1-515 H CH3 F N 4-chlorophenoxy 1-516 H CH3 F N 3-fluoro-4-methylphenoxy 1-517 H CH3 F N 3-methoxyphenoxy 1-518 H CH3 F N 3-fluoro-4-chlorophenoxy 1-519 H CH3 F N 4-methylphenoxy 1-520 H CH3 F N 4-fluoro-3-methoxyphenoxy 1-521 H CH3 F N 2,4-difluoro-3-methoxyphenoxy 1-522 H CH3 H N phenoxy 1-523 H CH3 H N 4-fluorophenoxy 1-524 H CH3 H N 3,4-difluorophenoxy 1-525 H CH3 H N 2,4-difluorophenoxy 1-526 H CH3 H N 4-chlorophenoxy 1-527 H CH3 H N 3-fluoro-4-methylphenoxy 1-528 H CH3 H N 3-methoxyphenoxy 1-529 H CH3 H N 3-fluoro-4-chlorophenoxy 1-530 H CH3 H N 4-methylphenoxy 1-531 H CH3 H N 4-fluoro-3-methoxyphenoxy 1-532 H CH3 H N 2,4-difluoro-3-methoxyphenoxy 1-533 H CH3 CF3 N phenoxy 1-534 H CH3 CF3 N 4-chlorophenoxy 1-535 H CH3 CF3 N 4-fluoro-3-methoxyphenoxy 1-536 CH3 CH3 Cl N phenoxy 1-537 CH3 CH3 Cl N 4-fluorophenoxy 1-538 CH3 CH3 Cl N 3,4-difluorophenoxy 1-539 CH3 CH3 Cl N 2,4-difluorophenoxy 1-540 CH3 CH3 Cl N 4-chlorophenoxy 1-541 CH3 CH3 Cl N 3-fluoro-4-methylphenoxy 1-542 CH3 CH3 Cl N 3-methoxyphenoxy 1-543 CH3 CH3 Cl N 3-fluoro-4-chlorophenoxy 1-544 CH3 CH3 Cl N 4-methylphenoxy 1-545 CH3 CH3 Cl N 4-fluoro-3-methoxyphenoxy 1-546 CH3 CH3 Cl N 2,4-difluoro-3-methoxyphenoxy 1-547 CH3 CH3 Cl CF phenoxy 1-548 CH3 CH3 Cl CF 4-fluorophenoxy 1-549 CH3 CH3 Cl CF 3,4-difluorophenoxy 1-550 CH3 CH3 Cl CF 2,4-difluorophenoxy 1-551 CH3 CH3 Cl CF 4-chlorophenoxy 1-552 CH3 CH3 Cl CF 3-fluoro-4-methylphenoxy 1-553 CH3 CH3 Cl CF 3-methoxyphenoxy 1-554 CH3 CH3 Cl CF 3-fluoro-4-chlorophenoxy 1-555 CH3 CH3 Cl CF 4-methylphenoxy 1-556 CH3 CH3 Cl CF 4-fluoro-3-methoxyphenoxy 1-557 CH3 CH3 Cl CF 2,4-difluoro-3-methoxyphenoxy 1-558 CH3 CH3 Cl CH phenoxy 1-559 CH3 CH3 Cl CH 4-fluorophenoxy 1-560 CH3 CH3 Cl CH 3,4-difluorophenoxy 1-561 CH3 CH3 Cl CH 2,4-difluorophenoxy 1-562 CH3 CH3 Cl CH 4-chlorophenoxy 1-563 CH3 CH3 Cl CH 3-fluoro-4-methylphenoxy 1-564 CH3 CH3 Cl CH 3-methoxyphenoxy 1-565 CH3 CH3 Cl CH 3-fluoro-4-chlorophenoxy 1-566 CH3 CH3 Cl CH 4-methylphenoxy 1-567 CH3 CH3 Cl CH 4-fluoro-3-methoxyphenoxy 1-568 CH3 CH3 Cl CH 2,4-difluoro-3-methoxyphenoxy 1-569 CH3 CH3 F N phenoxy 1-570 CH3 CH3 F N 4-fluorophenoxy 1-571 CH3 CH3 F N 3,4-difluorophenoxy 1-572 CH3 CH3 F N 2,4-difluorophenoxy 1-573 CH3 CH3 F N 4-chlorophenoxy 1-574 CH3 CH3 F N 3-fluoro-4-methylphenoxy 1-575 CH3 CH3 F N 3-methoxyphenoxy 1-576 CH3 CH3 F N 3-fluoro-4-chlorophenoxy 1-577 CH3 CH3 F N 4-methylphenoxy 1-578 CH3 CH3 F N 4-fluoro-3-methoxyphenoxy 1-579 CH3 CH3 F N 2,4-difluoro-3-methoxyphenoxy 1-580 CH3 CH3 H N phenoxy 1-581 CH3 CH3 H N 4-fluorophenoxy 1-582 CH3 CH3 H N 3,4-difluorophenoxy 1-583 CH3 CH3 H N 2,4-difluorophenoxy 1-584 CH3 CH3 H N 4-chlorophenoxy 1-585 CH3 CH3 H N 3-fluoro-4-methylphenoxy 1-586 CH3 CH3 H N 3-methoxyphenoxy 1-587 CH3 CH3 H N 3-fluoro-4-chlorophenoxy 1-588 CH3 CH3 H N 4-methylphenoxy 1-589 CH3 CH3 H N 4-fluoro-3-methoxyphenoxy 1-590 CH3 CH3 H N 2,4-difluoro-3-methoxyphenoxy 1-591 CH3 CH3 F N 5-chloro-3-fluoro-2-pyridyloxy 1-592 CH3 CH3 F N 5-chloro-2-pyridyloxy 1-593 CH3 CH3 F N 5-fluoro-2-pyridyloxy 1-594 CH3 CH3 F N 3,5-difluoro-2-pyridyloxy 1-595 CH3 CH3 F N 5-fluoro-2-pyrimidyloxy 1-596 CH3 CH3 F N 5-chloro-2-pyrimidyloxy 1-597 CH3 CH3 Cl N 5-chloro-3-fluoro-2-pyridyloxy 1-598 CH3 CH3 Cl N 5-chloro-2-pyridyloxy 1-599 CH3 CH3 Cl N 5-fluoro-2-pyridyloxy 1-600 CH3 CH3 Cl N 3,5-difluoro-2-pyridyloxy 1-601 CH3 CH3 Cl N 5-fluoro-2-pyrimidyloxy 1-602 CH3 CH3 Cl N 5-chloro-2-pyrimidyloxy 1-603 H CH3 F N 5-chloro-3-fluoro-2-pyridyloxy 1-604 H CH3 F N 5-chloro-2-pyridyloxy 1-605 H CH3 F N 5-fluoro-2-pyridyloxy 1-606 H CH3 F N 3,5-difluoro-2-pyridyloxy 1-607 H CH3 F N 5-fluoro-2-pyrimidyloxy 1-608 H CH3 F N 5-chloro-2-pyrimidyloxy 1-609 H CH3 Cl N 5-chloro-3-fluoro-2-pyridyloxy 1-610 H CH3 Cl N 5-chloro-2-pyridyloxy 1-611 H CH3 Cl N 5-fluoro-2-pyridyloxy 1-612 H CH3 Cl N 3,5-difluoro-2-pyridyloxy 1-613 H CH3 Cl N 5-fluoro-2-pyrimidyloxy 1-614 H CH3 Cl N 5-chloro-2-pyrimidyloxy 1-615 CH3 CH3 F CH 5-chloro-3-fluoro-2-pyridyloxy 1-616 CH3 CH3 F CH 5-chloro-2-pyridyloxy 1-617 CH3 CH3 F CH 5-fluoro-2-pyridyloxy 1-618 CH3 CH3 F CH 3,5-difluoro-2-pyridyloxy 1-619 CH3 CH3 F CH 5-fluoro-2-pyrimidyloxy 1-620 CH3 CH3 F CH 5-chloro-2-pyrimidyloxy 1-621 CH3 CH3 Cl CH 5-chloro-3-fluoro-2-pyridyloxy 1-622 CH3 CH3 Cl CH 5-chloro-2-pyridyloxy 1-623 CH3 CH3 Cl CH 5-fluoro-2-pyridyloxy 1-624 CH3 CH3 Cl CH 3,5-difluoro-2-pyridyloxy 1-625 CH3 CH3 Cl CH 5-fluoro-2-pyrimidyloxy 1-626 CH3 CH3 Cl CH 5-chloro-2-pyrimidyloxy 1-627 H CH3 F CH 5-chloro-3-fluoro-2-pyridyloxy 1-628 H CH3 F CH 5-chloro-2-pyridyloxy 1-629 H CH3 F CH 5-fluoro-2-pyridyloxy 1-630 H CH3 F CH 3,5-difluoro-2-pyridyloxy 1-631 H CH3 F CH 5-fluoro-2-pyrimidyloxy 1-632 H CH3 F CH 5-chloro-2-pyrimidyloxy 1-633 H CH3 Cl CH 5-chloro-3-fluoro-2-pyridyloxy 1-634 H CH3 Cl CH 5-chloro-2-pyridyloxy 1-635 H CH3 Cl CH 5-fluoro-2-pyridyloxy 1-636 H CH3 Cl CH 3,5-difluoro-2-pyridyloxy 1-637 H CH3 Cl CH 5-fluoro-2-pyrimidyloxy 1-638 H CH3 Cl CH 5-chloro-2-pyrimidyloxy 1-639 CH3 CH3 F CF 5-chloro-3-fluoro-2-pyridyloxy 1-640 CH3 CH3 F CF 5-chloro-2-pyridyloxy 1-641 CH3 CH3 F CF 5-fluoro-2-pyridyloxy 1-642 CH3 CH3 F CF 3,5-difluoro-2-pyridyloxy 1-643 CH3 CH3 F CF 5-fluoro-2-pyrimidyloxy 1-644 CH3 CH3 F CF 5-chloro-2-pyrimidyloxy 1-645 CH3 CH3 Cl CF 5-chloro-3-fluoro-2-pyridyloxy 1-646 CH3 CH3 Cl CF 5-chloro-2-pyridyloxy 1-647 CH3 CH3 Cl CF 5-fluoro-2-pyridyloxy 1-648 CH3 CH3 Cl CF 3,5-difluoro-2-pyridyloxy 1-649 CH3 CH3 Cl CF 5-fluoro-2-pyrimidyloxy 1-650 CH3 CH3 Cl CF 5-chloro-2-pyrimidyloxy 1-651 H CH3 F CF 5-chloro-3-fluoro-2-pyridyloxy 1-652 H CH3 F CF 5-chloro-2-pyridyloxy 1-653 H CH3 F CF 5-fluoro-2-pyridyloxy 1-654 H CH3 F CF 3,5-difluoro-2-pyridyloxy 1-655 H CH3 F CF 5-fluoro-2-pyrimidyloxy 1-656 H CH3 F CF 5-chloro-2-pyrimidyloxy 1-657 H CH3 Cl CF 5-chloro-3-fluoro-2-pyridyloxy 1-658 H CH3 Cl CF 5-chloro-2-pyridyloxy 1-659 H CH3 Cl CF 5-fluoro-2-pyridyloxy 1-660 H CH3 Cl CF 3,5-difluoro-2-pyridyloxy 1-661 H CH3 Cl CF 5-fluoro-2-pyrimidyloxy 1-662 H CH3 Cl CF 5-chloro-2-pyrimidyloxy

NMR Data of Selected Examples (End Products and Intermediates)
NMR Peak List Method

The 1H NMR data of selected examples are noted in the form of 1H NMR peak lists. For each signal peak, first the δ value in ppm and then the signal intensity in round brackets are listed. The δ value-signal intensity number pairs for different signal peaks are listed with separation from one another by semicolons.

The peak list for one example therefore takes the form of:

δ1 (intensity1); δ2 (intensity2); . . . ; δi (intensityi); . . . ; δn (intensityn)

The intensity of sharp signals correlates with the height of the signals in a printed example of an NMR spectrum in cm and shows the true ratios of the signal intensities. In the case of broad signals, several peaks or the middle of the signal and the relative intensity thereof may be shown in comparison to the most intense signal in the spectrum.

For calibration of the chemical shift of 1H NMR spectra we use tetramethylsilane and/or the chemical shift of the solvent, particularly in the case of spectra measured in DMSO. Therefore, the tetramethylsilane peak may but need not occur in NMR peak lists.

The lists of the 1H NMR peaks are similar to the conventional 1H NMR printouts and thus usually contain all peaks listed in a conventional NMR interpretation.

In addition, like conventional 1H NMR printouts, they may show solvent signals, signals of stereoisomers of the target compounds, which likewise form part of the subject matter of the invention, and/or peaks of impurities.

In the reporting of compound signals in the delta range of solvents and/or water, our lists of 1H NMR peaks show the usual solvent peaks, for example peaks of DMSO in DMSO-D6 and the peak of water, which usually have a high intensity on average.

The peaks of stereoisomers of the target compounds and/or peaks of impurities usually have a lower intensity on average than the peaks of the target compounds (for example with a purity of >90%).

Such stereoisomers and/or impurities may be typical of the particular preparation process. Their peaks can thus help in identifying reproduction of our preparation process with reference to “by-product fingerprints”.

An expert calculating the peaks of the target compounds by known methods (MestreC, ACD simulation, but also with empirically evaluated expected values) can, if required, isolate the peaks of the target compounds, optionally using additional intensity filters. This isolation would be similar to the relevant peak picking in conventional 1H NMR interpretation.

Further details of 1H NMR peak lists can be found in the Research Disclosure Database Number 564025.

Example number I-397: 1H-NMR(400.6 MHz, CDCl3): δ = 8.4126 (16.0); 7.4745 (1.9); 7.4555 (2.1); 7.2599 (44.6); 7.2276 (0.6); 7.2234 (0.9); 7.2119 (0.7); 7.2073 (2.6); 7.2030 (1.6); 7.1923 (1.1); 7.1887 (2.8); 7.1865 (2.0); 7.1831 (0.6); 7.1660 (1.1); 7.1624 (1.1); 7.1487 (1.7); 7.1447 (2.9); 7.1404 (3.1); 7.1341 (0.7); 7.1297 (0.9); 7.1283 (1.0); 7.1243 (1.8); 7.1207 (1.2); 7.0382 (1.9); 7.0193 (1.8); 3.9295 (5.8); 2.4678 (12.8); 0.8821 (0.9); 0.0080 (0.7); −0.0002 (26.5); −0.0085 (0.8) Example number I-400: 1H-NMR(400.0 MHz, CDCl3): δ = 8.4920 (0.7); 8.4616 (16.0); 7.5009 (1.1); 7.4831 (1.2); 7.2607 (14.0); 7.1218 (0.5); 7.1171 (0.8); 7.1010 (0.8); 7.0423 (1.8); 7.0226 (1.6); 6.7585 (0.7); 6.7424 (0.6); 6.7356 (2.2); 6.7143 (2.2); 6.7075 (0.7); 6.6955 (0.5); 3.9163 (3.9); 2.6147 (0.7); 2.4569 (11.0); 1.5563 (6.0); 0.0080 (0.7); −0.0002 (18.4); −0.0085 (0.7) Example number I-405: 1H-NMR(400.0 MHz, CDCl3): δ = 8.4073 (9.2); 7.4640 (1.2); 7.4450 (1.3); 7.2592 (4.8); 7.0275 (1.4); 7.0099 (16.0); 3.8797 (3.9); 2.4635 (7.8); 2.2781 (8.8); 1.5678 (1.0); 1.2644 (1.0); 0.8818 (1.6); 0.8641 (0.6); −0.0002 (6.2) Example number I-406: 1H-NMR(400.0 MHz, CDCl3): δ = 8.4666 (2.2); 8.4474 (13.6); 8.4354 (2.2); 7.4577 (1.5); 7.4387 (1.6); 7.2621 (5.0); 7.0416 (1.8); 7.0234 (1.9); 6.9381 (1.1); 6.9175 (1.4); 6.9100 (1.2); 6.8894 (1.3); 6.7666 (0.8); 6.7614 (0.9); 6.7462 (0.8); 6.7410 (0.9); 6.6779 (0.6); 6.6726 (0.5); 6.6672 (0.6); 6.6619 (0.6); 6.6573 (0.5); 5.2978 (5.0); 3.9432 (0.6); 3.8883 (4.0); 3.8769 (0.5); 3.8064 (16.0); 2.4663 (10.3); 1.5924 (1.5); −0.0002 (6.4) Example number I-408: 1H-NMR(400.0 MHz, CDCl3): δ = 8.1461 (2.7); 8.1394 (2.8); 7.6547 (2.4); 7.6480 (2.3); 7.6330 (2.5); 7.6263 (2.4); 7.5189 (0.5); 7.4023 (2.4); 7.3834 (2.6); 7.2765 (1.3); 7.2731 (1.9); 7.2601 (96.5); 7.2412 (1.7); 7.2376 (3.3); 7.2030 (1.4); 7.1998 (1.3); 7.1818 (3.9); 7.1780 (3.9); 7.1613 (2.6); 6.9961 (0.5); 6.9479 (2.7); 6.9333 (3.6); 6.9320 (3.8); 6.9294 (2.6); 6.9116 (3.1); 3.9289 (7.8); 2.4189 (16.0); 1.5469 (6.8); 1.3331 (0.8); 1.2843 (1.3); 1.2556 (2.6); 0.8803 (0.5); 0.0693 (0.9); 0.0080 (2.1); −0.0002 (56.5); −0.0084 (2.0) Example number I-419: 1H-NMR(400.0 MHz, CDCl3): δ = 8.0098 (4.6); 8.0042 (4.7); 7.5250 (2.6); 7.5194 (2.5); 7.5030 (2.6); 7.4975 (2.5); 7.3706 (2.4); 7.3518 (2.6); 7.2938 (0.9); 7.2909 (1.4); 7.2870 (0.7); 7.2752 (2.4); 7.2726 (3.3); 7.2700 (2.5); 7.2590 (46.7); 7.2549 (4.4); 7.2206 (4.6); 7.2142 (2.3); 7.2033 (2.2); 7.1999 (2.0); 7.1939 (1.8); 7.1762 (0.6); 6.9001 (2.6); 6.8813 (2.4); 4.0053 (7.5); 2.3544 (16.0); 1.5571 (0.7); 0.0080 (0.9); −0.0002 (27.1); −0.0085 (0.8) Example number I-422: 1H-NMR(400.0 MHz, CDCl3): δ = 8.0272 (4.3); 8.0217 (4.4); 7.5377 (2.4); 7.5322 (2.3); 7.5158 (2.4); 7.5103 (2.3); 7.4161 (1.8); 7.3974 (1.9); 7.2594 (8.4); 7.2012 (0.5); 7.1799 (1.0); 7.1635 (1.0); 7.1423 (0.5); 6.9107 (2.6); 6.8918 (2.4); 6.8008 (0.7); 6.7957 (1.8); 6.7799 (1.0); 6.7747 (4.4); 6.7539 (2.0); 6.7485 (0.7); 3.9888 (5.7); 2.3449 (16.0); 1.5493 (2.5); −0.0002 (11.1) Example number I-428: 1H-NMR(400.0 MHz, CDCl3): δ = 8.0312 (2.8); 8.0256 (2.8); 7.5443 (1.6); 7.5388 (1.6); 7.5224 (1.6); 7.5168 (1.8); 7.3747 (1.5); 7.3558 (1.6); 7.2598 (6.4); 7.0774 (0.5); 6.9912 (1.2); 6.9706 (1.4); 6.9630 (1.2); 6.9425 (1.4); 6.9081 (1.6); 6.8893 (1.4); 6.8642 (0.8); 6.8589 (0.9); 6.8437 (0.8); 6.8385 (0.9); 6.7491 (0.6); 6.7438 (0.5); 6.7384 (0.6); 6.7331 (0.5); 5.2978 (1.2); 4.0080 (0.6); 3.9614 (4.1); 3.9013 (0.6); 3.8296 (16.0); 2.3531 (10.9); 2.1042 (0.8); 1.5523 (1.8); −0.0002 (9.0) Example number I-430: 1H-NMR(400.0 MHz, CDCl3): δ = 8.3534 (16.0); 7.4614 (2.1); 7.4424 (2.3); 7.2596 (14.7); 7.2329 (0.7); 7.2298 (1.0); 7.2253 (0.7); 7.2185 (0.8); 7.2143 (1.4); 7.2112 (2.3); 7.2086 (2.0); 7.2060 (1.5); 7.1941 (3.4); 7.1628 (2.6); 7.1575 (3.9); 7.1461 (1.9); 7.1389 (2.1); 7.1290 (0.7); 7.0181 (2.2); 6.9993 (2.0); 3.9447 (6.6); 2.4534 (13.9); 2.4350 (0.7); 1.5586 (3.8); 1.2635 (0.5); 0.8819 (0.9); 0.0080 (0.7); −0.0002 (19.6); −0.0085 (0.8) Example number I-433: 1H-NMR(400.6 MHz, CDCl3): δ = 8.3968 (16.0); 7.4932 (1.6); 7.4743 (1.7); 7.2612 (12.4); 7.1528 (0.6); 7.1364 (0.7); 7.1317 (1.0); 7.1156 (1.0); 7.0242 (2.4); 7.0051 (2.2); 6.7670 (0.7); 6.7606 (0.9); 6.7447 (0.8); 6.7381 (3.1); 6.7311 (0.5); 6.7170 (2.9); 6.7130 (1.0); 6.6985 (0.6); 6.6961 (0.6); 3.9314 (5.3); 2.6154 (0.6); 2.4432 (14.9); 1.5644 (6.7); 0.0079 (0.5); −0.0002 (15.7) Example number I-438: 1H-NMR(400.0 MHz, CDCl3): δ = 8.6597 (1.1); 8.6476 (1.1); 8.3605 (16.0); 7.4435 (2.2); 7.4245 (2.4); 7.2891 (0.9); 7.2770 (0.5); 7.2599 (9.2); 7.0509 (0.7); 7.0285 (13.9); 7.0049 (2.8); 6.9856 (2.1); 3.8948 (6.8); 2.4478 (14.1); 2.3200 (0.6); 2.2784 (14.7); 1.5765 (4.9); 0.0080 (0.5); −0.0002 (11.6); −0.0085 (0.5) Example number I-439: 1H-NMR(400.6 MHz, CDCl3): δ = 8.3861 (11.0); 7.4483 (1.5); 7.4294 (1.6); 7.2610 (16.4); 7.0240 (1.6); 7.0050 (1.5); 6.9428 (1.1); 6.9222 (1.3); 6.9147 (1.1); 6.8942 (1.3); 6.7867 (0.8); 6.7815 (0.9); 6.7663 (0.8); 6.7612 (0.9); 6.6915 (0.6); 6.6862 (0.5); 6.6809 (0.6); 6.6755 (0.5); 5.2998 (0.7); 3.9053 (4.3); 3.8096 (16.0); 2.6155 (0.8); 2.4527 (10.1); 1.5528 (9.5); 0.0080 (0.6); −0.0002 (22.2); −0.0085 (0.6) Example number I-441: 1H-NMR(400.6 MHz, CDCl3): δ = 8.5217 (10.9); 8.5097 (11.2); 7.4457 (2.4); 7.4267 (2.6); 7.2609 (8.3); 7.2326 (0.8); 7.2296 (1.3); 7.2256 (0.6); 7.2143 (2.1); 7.2115 (3.1); 7.2085 (2.3); 7.1995 (1.2); 7.1940 (4.0); 7.1920 (2.8); 7.1896 (1.0); 7.1717 (1.8); 7.1667 (4.7); 7.1605 (2.4); 7.1538 (1.3); 7.1500 (2.0); 7.1475 (1.7); 7.1463 (1.8); 7.1403 (1.7); 7.1229 (0.6); 7.0205 (5.7); 7.0085 (6.7); 7.0028 (2.5); 6.9966 (3.4); 3.9298 (7.3); 2.4743 (16.0); 2.2314 (0.6); 1.6132 (1.1); −0.0002 (10.9) Example number I-444: 1H-NMR(400.6 MHz, CDCl3): δ = 8.5368 (9.8); 8.5249 (10.0); 7.5029 (1.6); 7.4840 (1.7); 7.2617 (14.4); 7.1513 (0.6); 7.1351 (0.7); 7.1300 (1.2); 7.1139 (1.2); 7.1092 (0.7); 7.0931 (0.6); 7.0505 (2.9); 7.0386 (7.9); 7.0265 (2.9); 7.0206 (2.4); 6.7494 (0.7); 6.7431 (0.9); 6.7270 (0.8); 6.7201 (1.2); 6.7189 (1.2); 6.7115 (0.9); 6.7094 (0.7); 6.7027 (0.9); 6.6964 (1.0); 6.6909 (1.5); 6.6890 (1.2); 6.6841 (0.8); 6.6823 (0.8); 6.6703 (0.6); 6.6677 (0.6); 5.2994 (0.7); 3.9190 (5.4); 3.7973 (0.7); 2.6160 (0.6); 2.4707 (16.0); 2.2526 (1.7); 1.5844 (3.3); 0.0079 (0.5); −0.0002 (19.3); −0.0085 (0.5) Example number I-449: 1H-NMR(400.6 MHz, CDCl3): δ = 8.5315 (6.5); 8.5196 (6.7); 7.4264 (2.5); 7.4074 (2.7); 7.2602 (14.5); 7.0621 (1.6); 7.0415 (7.8); 7.0307 (8.1); 7.0167 (4.7); 7.0080 (4.4); 6.9887 (2.6); 3.8803 (8.4); 2.6148 (0.7); 2.4689 (16.0); 2.3180 (0.5); 2.2755 (15.4); 2.0451 (0.7); 1.5621 (8.8); −0.0002 (18.2) Example number I-450: 1H-NMR(400.6 MHz, CDCl3): δ = 8.5201 (5.7); 8.5081 (5.9); 7.4597 (1.4); 7.4407 (1.6); 7.2614 (15.7); 7.0393 (3.3); 7.0273 (3.6); 7.0210 (1.4); 7.0153 (1.8); 6.9226 (1.1); 6.9020 (1.4); 6.8945 (1.1); 6.8739 (1.3); 6.7733 (0.8); 6.7682 (0.8); 6.7530 (0.8); 6.7478 (0.8); 6.6884 (0.5); 6.6777 (0.6); 6.6723 (0.5); 3.8927 (3.9); 3.7941 (16.0); 2.6156 (0.7); 2.4805 (9.5); 1.5632 (7.5); 0.0080 (0.6); −0.0002 (20.8); −0.0085 (0.6) Example number I-455: 1H-NMR(400.0 MHz, CDCl3): δ = 8.2100 (1.2); 8.2083 (1.3); 8.2051 (1.3); 8.2033 (1.3); 8.1976 (1.3); 8.1958 (1.3); 8.1926 (1.3); 8.1909 (1.2); 7.7177 (1.2); 7.7126 (1.2); 7.6995 (1.4); 7.6970 (1.4); 7.6945 (1.4); 7.6920 (1.3); 7.6790 (1.3); 7.6739 (1.2); 7.4298 (1.7); 7.4108 (1.8); 7.2603 (15.5); 7.1692 (0.6); 7.1486 (1.2); 7.1326 (1.2); 7.1259 (0.7); 7.1099 (0.5); 7.0439 (1.3); 7.0416 (1.4); 7.0314 (1.3); 7.0292 (1.4); 7.0258 (1.3); 7.0236 (1.3); 7.0134 (1.2); 7.0111 (1.3); 6.9772 (1.6); 6.9753 (2.6); 6.9545 (2.8); 6.9519 (3.2); 6.9319 (2.4); 6.7765 (0.6); 6.7703 (1.1); 6.7617 (0.9); 6.7548 (0.9); 6.7457 (1.6); 6.7416 (1.8); 6.7349 (0.8); 6.7287 (0.7); 6.7224 (1.6); 3.9234 (5.7); 2.4218 (16.0); 1.5573 (2.7); 1.3334 (0.7); 1.2843 (0.9); 1.2555 (1.1); 1.1374 (0.6); 1.1216 (0.6); 0.9169 (0.6); 0.0079 (0.6); −0.0002 (21.3); −0.0084 (0.7) Example number I-461: 1H-NMR(400.0 MHz, CDCl3): δ = 8.2153 (0.8); 8.2136 (0.9); 8.2104 (0.9); 8.2086 (0.9); 8.2029 (0.9); 8.2011 (0.9); 8.1979 (0.9); 8.1961 (0.8); 7.7182 (0.8); 7.7132 (0.8); 7.7001 (1.0); 7.6976 (1.0); 7.6951 (1.0); 7.6926 (0.9); 7.6795 (0.9); 7.6745 (0.9); 7.3943 (1.6); 7.3754 (1.7); 7.2618 (8.4); 7.0473 (0.9); 7.0449 (1.0); 7.0348 (1.0); 7.0325 (1.0); 7.0292 (1.0); 7.0269 (1.0); 7.0167 (0.9); 7.0144 (0.9); 6.9747 (1.1); 6.9726 (2.1); 6.9708 (2.2); 6.9541 (2.8); 6.9522 (3.0); 6.9503 (2.5); 6.9426 (1.3); 6.9352 (1.6); 6.9221 (1.3); 6.8121 (0.9); 6.8070 (1.0); 6.7917 (0.9); 6.7866 (0.9); 6.7176 (0.6); 6.7123 (0.5); 6.7068 (0.6); 6.7016 (0.6); 6.6970 (0.5); 3.9040 (2.2); 3.8909 (4.5); 3.7903 (16.0); 2.4325 (10.4); 1.5784 (0.9); 1.3335 (1.0); 1.2844 (1.4); 1.2544 (1.4); 0.0701 (0.6); −0.0002 (11.7) Example number I-463: 1H-NMR(400.0 MHz, CDCl3): δ = 8.6554 (7.9); 8.6537 (7.4); 7.5432 (2.4); 7.5241 (2.6); 7.2596 (12.0); 7.1822 (0.7); 7.1779 (1.0); 7.1739 (0.6); 7.1622 (2.2); 7.1537 (1.1); 7.1474 (1.6); 7.1433 (3.4); 7.1378 (1.2); 7.1249 (1.5); 7.1212 (1.7); 7.1065 (4.6); 7.1003 (4.7); 7.0861 (2.5); 7.0804 (3.0); 3.9282 (7.6); 2.4964 (16.0); 1.5535 (5.1); 1.2642 (0.6); 0.8820 (0.9); 0.0080 (0.6); −0.0002 (15.7); −0.0084 (0.7) Example number I-464: 1H-NMR(400.0 MHz, CDCl3): δ = 8.7268 (7.6); 8.7250 (7.7); 7.5564 (1.7); 7.5376 (1.8); 7.2622 (3.8); 7.1092 (0.7); 7.0989 (2.7); 7.0936 (1.0); 7.0880 (1.5); 7.0798 (2.6); 7.0720 (1.4); 7.0671 (0.8); 7.0507 (0.6); 6.7407 (0.8); 6.7343 (0.9); 6.7185 (0.9); 6.7158 (0.8); 6.7120 (1.2); 6.7097 (1.2); 6.6987 (0.9); 6.6963 (0.9); 6.6931 (1.0); 6.6875 (1.2); 6.6781 (1.4); 6.6697 (0.9); 6.6576 (0.6); 6.6550 (0.6); 5.2973 (2.4); 3.9126 (5.9); 2.4857 (16.0); 1.5978 (1.6); −0.0002 (4.9) Example number I-465: 1H-NMR(400.0 MHz, CDCl3): δ = 8.7729 (0.7); 8.7710 (0.7); 8.7201 (1.0); 8.7182 (1.1); 8.7145 (2.2); 8.7128 (5.0); 8.7108 (5.0); 7.5117 (1.5); 7.4927 (1.6); 7.2618 (5.5); 7.1002 (1.7); 7.0810 (1.4); 6.9077 (1.1); 6.8871 (1.4); 6.8797 (1.2); 6.8591 (1.3); 6.7348 (0.8); 6.7296 (0.9); 6.7145 (0.8); 6.7094 (0.9); 6.6496 (0.6); 6.6442 (0.6); 6.6389 (0.6); 6.6336 (0.6); 6.6290 (0.5); 6.6183 (0.5); 5.2983 (2.6); 3.9502 (0.5); 3.8841 (4.1); 3.7972 (16.0); 2.4965 (10.2); 1.5761 (2.2); −0.0002 (7.4) Example number I-466: 1H-NMR(400.6 MHz, CDCl3): δ = 8.6395 (7.7); 8.6376 (7.6); 7.5432 (2.4); 7.5242 (2.6); 7.2598 (11.0); 7.0935 (2.5); 7.0745 (2.3); 6.9820 (0.9); 6.9679 (0.7); 6.9606 (9.1); 6.9557 (8.2); 6.9485 (0.7); 6.9346 (0.8); 5.2979 (0.5); 3.8809 (7.1); 2.4944 (16.0); 2.2372 (15.0); 1.5642 (4.2); −0.0002 (14.8) Example number I-478: 1H-NMR(400.0 MHz, CDCl3): δ = 8.3304 (9.7); 7.2604 (36.0); 7.1866 (0.8); 7.1714 (1.4); 7.1685 (2.0); 7.1655 (1.6); 7.1567 (0.9); 7.1511 (2.6); 7.1275 (3.2); 7.1196 (1.5); 7.1110 (1.6); 7.0990 (1.2); 6.9298 (2.6); 4.0222 (5.1); 2.4285 (11.2); 2.2802 (10.8); 1.5519 (16.0); 0.0080 (1.0); −0.0002 (25.2); −0.0085 (1.2) Example number I-479: 1H-NMR(400.6 MHz, CDCl3): δ = 8.3622 (15.6); 7.2608 (10.7); 7.1105 (1.6); 7.1050 (0.7); 7.0971 (1.9); 7.0885 (2.0); 7.0807 (0.8); 7.0751 (2.0); 6.9261 (3.4); 6.8864 (2.6); 6.8810 (0.8); 6.8699 (0.8); 6.8647 (4.7); 6.8593 (0.8); 6.8482 (0.7); 6.8428 (2.0); 3.9866 (5.6); 2.4224 (16.0); 2.2686 (15.0); 1.5651 (1.6); −0.0002 (14.7) Example number I-481: 1H-NMR(400.6 MHz, CDCl3): δ = 8.4357 (2.3); 8.3706 (16.0); 7.2620 (35.2); 7.0106 (0.5); 6.9903 (1.0); 6.9724 (1.0); 6.9685 (0.7); 6.9513 (0.6); 6.9367 (3.4); 6.7478 (0.7); 6.7414 (0.9); 6.7243 (1.4); 6.7168 (1.1); 6.7004 (0.7); 6.6940 (0.9); 6.6767 (0.5); 6.6595 (0.7); 6.6553 (0.6); 6.6492 (0.6); 6.6382 (0.7); 3.9744 (5.0); 2.4566 (2.2); 2.4217 (15.0); 2.3602 (2.2); 2.2722 (14.3); 1.5808 (5.0); 0.0700 (0.6); 0.0079 (0.6); 0.0022 (0.8); −0.0002 (20.7); −0.0085 (0.6) Example number I-482: 1H-NMR(400.6 MHz, CDCl3): δ = 8.4352 (1.3); 8.3637 (15.9); 7.2614 (35.5); 7.1576 (3.8); 7.1526 (1.4); 7.1415 (1.6); 7.1363 (6.3); 7.1303 (1.0); 7.0824 (0.7); 7.0765 (4.6); 7.0713 (1.4); 7.0600 (1.0); 7.0550 (2.7); 6.9256 (3.7); 5.1087 (0.5); 4.8590 (0.6); 3.9874 (7.1); 2.4564 (1.4); 2.4217 (16.0); 2.3599 (1.4); 2.2581 (15.5); 1.5745 (9.7); 0.0079 (0.6); −0.0002 (21.8); −0.0085 (0.7) Example number I-483: 1H-NMR(400.6 MHz, CDCl3): δ = 8.4352 (0.8); 8.3570 (15.4); 7.2610 (25.8); 7.2560 (0.5); 6.9913 (0.8); 6.9719 (1.8); 6.9515 (1.1); 6.9267 (3.6); 6.8122 (1.2); 6.8084 (1.5); 6.7891 (1.3); 6.7785 (1.3); 6.7516 (1.2); 3.9725 (6.3); 2.4564 (0.9); 2.4270 (16.0); 2.3596 (0.9); 2.2644 (16.0); 2.2407 (0.5); 2.2359 (0.6); 2.1720 (6.9); 2.1682 (7.1); 1.5715 (2.6); 0.0079 (0.5); −0.0002 (18.5); −0.0085 (0.5) Example number I-484: 1H-NMR(400.6 MHz, CDCl3): δ = 8.4351 (0.6); 8.3328 (8.5); 7.2611 (29.3); 7.1072 (0.8); 7.0877 (1.6); 7.0681 (1.0); 6.9238 (2.2); 6.7166 (0.9); 6.6976 (0.9); 6.6781 (0.7); 6.6730 (1.3); 6.6696 (1.1); 6.6602 (1.0); 6.6553 (0.5); 6.6403 (0.7); 6.6349 (0.5); 3.9943 (4.2); 3.8752 (0.8); 3.8210 (1.4); 3.7870 (0.9); 3.7830 (0.9); 3.7201 (16.0); 2.4565 (0.6); 2.4259 (8.9); 2.3598 (0.7); 2.2827 (9.7); 1.5771 (6.2); −0.0002 (18.7); −0.0085 (0.6) Example number I-485: 1H-NMR(400.6 MHz, CDCl3): δ = 8.4354 (2.2); 8.3826 (15.4); 7.2619 (26.2); 7.2194 (1.7); 7.1994 (2.7); 7.1798 (1.8); 6.9444 (1.2); 6.9392 (1.7); 6.9337 (3.6); 6.9192 (1.1); 6.9144 (1.4); 6.8956 (1.4); 6.8938 (1.4); 6.8906 (1.1); 6.8888 (1.0); 6.8752 (1.1); 6.8732 (1.2); 6.8702 (1.0); 6.8683 (0.9); 3.9986 (7.2); 2.4565 (2.0); 2.4245 (14.8); 2.3599 (2.3); 2.2570 (16.0); 1.5769 (2.7); −0.0002 (18.0); −0.0085 (0.5) Example number I-486: 1H-NMR(400.6 MHz, CDCl3): δ = 8.4346 (0.6); 8.3357 (15.1); 7.2597 (22.1); 7.0216 (1.7); 7.0063 (1.2); 7.0009 (5.4); 6.9824 (5.2); 6.9621 (1.7); 6.9183 (3.6); 3.9719 (6.5); 2.4563 (0.6); 2.4238 (15.2); 2.3591 (0.6); 2.2717 (16.0); 2.2509 (13.1); 1.5805 (3.6); −0.0002 (14.0) Example number I-487: 1H-NMR(400.6 MHz, CDCl3): δ = 8.3689 (11.0); 7.2611 (16.2); 6.9227 (2.3); 6.9010 (1.2); 6.8803 (1.4); 6.8729 (1.2); 6.8523 (1.4); 6.8021 (0.8); 6.7969 (0.8); 6.7817 (0.8); 6.7765 (0.8); 6.6478 (0.5); 6.6371 (0.6); 6.6318 (0.5); 5.2996 (1.3); 3.9786 (3.7); 3.9631 (0.8); 3.9052 (1.2); 3.7972 (16.0); 2.4208 (10.6); 2.2773 (10.2); 1.5600 (2.4); 1.2693 (1.2); 1.2417 (10.4); 0.0080 (0.6); −0.0002 (21.8); −0.0085 (0.6) Example number I-488: 1H-NMR(400.6 MHz, CDCl3): δ = 8.3778 (11.6); 7.2604 (50.3); 6.9349 (2.2); 6.6756 (0.7); 6.6716 (1.2); 6.6500 (0.8); 6.6462 (1.0); 6.6426 (0.6); 6.6273 (0.7); 6.6235 (0.6); 6.6089 (0.5); 3.9711 (3.0); 3.9592 (5.3); 3.9568 (8.6); 3.9543 (5.4); 2.4213 (10.2); 2.2693 (9.2); 1.5396 (16.0); 0.0079 (1.9); 0.0064 (0.6); 0.0047 (0.6); 0.0038 (0.8); −0.0002 (67.5); −0.0027 (3.6); −0.0051 (1.4); −0.0068 (0.8); −0.0084 (2.2) Example number I-500: 1H-NMR(400.6 MHz, CDCl3): δ = 9.3392 (0.7); 8.4924 (1.0); 8.4380 (16.0); 7.2995 (1.7); 7.2975 (0.7); 7.2939 (0.9); 7.2912 (2.7); 7.2831 (1.0); 7.2809 (2.8); 7.2779 (2.3); 7.2711 (3.3); 7.2642 (1.2); 7.2609 (15.5); 7.1007 (0.6); 7.0980 (1.3); 7.0953 (0.7); 7.0812 (3.1); 7.0798 (3.9); 7.0760 (0.7); 7.0611 (2.8); 7.0600 (2.1); 6.9371 (2.6); 6.9342 (3.3); 6.9325 (1.5); 6.9289 (0.8); 6.9202 (0.8); 6.9179 (1.4); 6.9152 (2.6); 6.9127 (2.4); 2.5272 (14.5); 1.5552 (2.8); 0.0080 (0.6); −0.0002 (20.3); −0.0085 (0.5) Example number I-504: 1H-NMR(400.6 MHz, CDCl3): δ = 8.4479 (9.3); 7.3151 (3.8); 7.2949 (4.5); 7.2618 (26.8); 7.2540 (0.8); 7.2456 (7.1); 7.2400 (2.2); 7.2288 (2.2); 7.2231 (7.9); 7.2147 (0.8); 7.1095 (0.9); 7.0892 (0.8); 6.8825 (0.7); 6.8741 (7.8); 6.8685 (2.3); 6.8572 (2.1); 6.8516 (6.8); 6.8432 (0.6); 5.2996 (2.7); 2.5303 (16.0); 1.2709 (0.7); −0.0002 (16.8); −0.0085 (0.6) Example number I-509: 1H-NMR(400.6 MHz, CDCl3): δ = 8.4775 (0.7); 8.4589 (12.9); 8.4312 (0.7); 8.2355 (1.1); 7.2762 (2.0); 7.2614 (33.7); 7.2561 (3.0); 7.0847 (1.8); 7.0836 (1.7); 7.0645 (1.5); 7.0633 (1.4); 6.9882 (1.3); 6.9661 (1.4); 6.9611 (1.3); 6.9391 (1.4); 6.6034 (1.0); 6.5963 (1.1); 6.5857 (1.0); 6.5786 (1.1); 6.4525 (0.8); 6.4451 (0.9); 6.4439 (0.9); 6.4367 (0.7); 6.4304 (0.7); 6.4230 (0.8); 6.4219 (0.8); 6.4146 (0.6); 5.3002 (0.9); 3.8103 (16.0); 2.5221 (11.6); 1.5594 (1.5); 1.2423 (0.6); 0.0080 (0.7); −0.0002 (25.2); −0.0085 (0.8) Example number I-511: 1H-NMR(400.6 MHz, CDCl3): δ = 8.3677 (7.5); 7.3039 (3.7); 7.2978 (2.4); 7.2925 (1.0); 7.2837 (4.3); 7.2791 (3.8); 7.2763 (3.3); 7.2703 (0.6); 7.2609 (64.6); 7.2580 (6.1); 7.2517 (1.1); 7.0980 (0.8); 7.0954 (1.6); 7.0927 (1.0); 7.0770 (3.2); 7.0610 (1.5); 7.0585 (2.0); 7.0559 (1.1); 6.9387 (0.5); 6.9350 (3.3); 6.9321 (4.3); 6.9268 (1.1); 6.9180 (1.0); 6.9158 (1.8); 6.9130 (3.5); 6.9106 (3.1); 2.5267 (16.0); 0.0079 (1.0); −0.0002 (38.5); −0.0085 (1.3) Example number I-515: 1H-NMR(400.6 MHz, CDCl3): δ = 8.3703 (10.4); 7.3132 (3.1); 7.2931 (3.7); 7.2614 (57.4); 7.2483 (0.6); 7.2398 (5.8); 7.2343 (1.9); 7.2230 (1.8); 7.2173 (6.6); 7.2090 (0.6); 7.0925 (1.6); 7.0724 (1.4); 6.8803 (0.6); 6.8719 (6.4); 6.8662 (1.9); 6.8550 (1.7); 6.8494 (5.7); 6.8410 (0.5); 2.5225 (16.0); 1.6803 (1.4); 0.0080 (0.8); −0.0002 (32.2); −0.0085 (1.1) Example number I-520: 1H-NMR(400.6 MHz, CDCl3): δ = 8.4016 (0.7); 8.3853 (11.2); 7.2786 (2.0); 7.2617 (27.4); 7.2586 (3.3); 7.0742 (1.7); 7.0731 (1.7); 7.0540 (1.4); 7.0529 (1.4); 6.9835 (1.3); 6.9614 (1.4); 6.9565 (1.3); 6.9344 (1.4); 6.6065 (1.0); 6.5994 (1.1); 6.5887 (1.0); 6.5817 (1.1); 6.4500 (0.8); 6.4427 (0.8); 6.4415 (1.0); 6.4342 (0.7); 6.4279 (0.7); 6.4207 (0.8); 6.4194 (0.8); 6.4121 (0.7); 3.8090 (16.0); 3.3772 (0.7); 2.5155 (11.1); 1.5591 (2.4); 1.2422 (3.5); 0.0079 (0.5); −0.0002 (19.7); −0.0085 (0.6) Example number I-522: 1H-NMR(400.6 MHz, CDCl3): δ = 8.5411 (6.9); 8.5290 (7.1); 7.3072 (2.9); 7.2868 (5.3); 7.2812 (0.9); 7.2701 (1.1); 7.2680 (3.1); 7.2648 (2.9); 7.2611 (17.7); 7.2514 (1.1); 7.2464 (2.8); 7.0873 (3.0); 7.0864 (2.7); 7.0848 (2.4); 7.0819 (1.0); 7.0661 (4.0); 7.0504 (0.6); 7.0477 (1.0); 7.0448 (0.7); 7.0426 (2.3); 7.0306 (4.4); 7.0185 (2.2); 6.9412 (0.5); 6.9377 (3.0); 6.9349 (3.7); 6.9332 (1.8); 6.9295 (1.0); 6.9208 (0.9); 6.9185 (1.6); 6.9158 (3.0); 6.9133 (2.7); 2.5417 (16.0); 0.0080 (0.6); −0.0002 (19.5); −0.0085 (0.6) Example number I-526: 1H-NMR(400.0 MHz, CDCl3): δ = 8.5167 (3.0); 8.5048 (3.0); 7.3095 (3.1); 7.2894 (3.8); 7.2607 (62.8); 7.2269 (0.5); 7.2185 (5.4); 7.2129 (1.7); 7.2017 (1.8); 7.1960 (6.3); 7.1876 (0.6); 7.0937 (1.2); 7.0736 (1.0); 7.0277 (1.7); 7.0157 (3.3); 7.0037 (1.6); 6.8780 (0.6); 6.8696 (6.2); 6.8640 (1.7); 6.8527 (1.6); 6.8471 (5.4); 2.5373 (16.0); 2.0449 (0.5); 1.5503 (12.3); 1.2420 (7.6); 0.0080 (1.4); −0.0002 (43.6); −0.0085 (1.2) Example number I-531: 1H-NMR(400.6 MHz, CDCl3): δ = 8.5339 (5.6); 8.5220 (5.7); 7.2798 (2.0); 7.2612 (46.5); 7.0778 (1.7); 7.0575 (1.4); 7.0405 (1.7); 7.0285 (3.3); 7.0166 (1.6); 6.9665 (1.3); 6.9444 (1.4); 6.9394 (1.3); 6.9173 (1.4); 6.6006 (1.0); 6.5936 (1.1); 6.5828 (1.0); 6.5757 (1.1); 6.4582 (0.8); 6.4496 (0.9); 6.4424 (0.7); 6.4361 (0.7); 6.4288 (0.8); 6.4276 (0.8); 6.4204 (0.6); 3.7962 (16.0); 2.5323 (11.2); 1.5523 (5.9); 0.0079 (0.9); −0.0002 (34.7); −0.0085 (1.1) Example number I-533: 1H-NMR(400.6 MHz, CDCl3): δ = 8.7378 (6.5); 8.7358 (6.5); 7.3171 (2.9); 7.3004 (2.0); 7.2968 (3.8); 7.2842 (1.0); 7.2819 (3.1); 7.2788 (2.6); 7.2653 (1.2); 7.2605 (30.6); 7.2544 (0.6); 7.1207 (2.4); 7.1196 (2.4); 7.1054 (0.8); 7.1025 (1.9); 7.1001 (2.6); 7.0877 (0.8); 7.0859 (0.9); 7.0842 (2.2); 7.0805 (0.7); 7.0684 (0.6); 7.0657 (1.1); 7.0629 (0.6); 6.9347 (3.0); 6.9319 (3.9); 6.9300 (1.8); 6.9265 (1.0); 6.9178 (0.9); 6.9155 (1.6); 6.9128 (3.0); 6.9103 (2.8); 2.5434 (16.0); 1.5436 (3.6); 0.0080 (1.0); −0.0002 (36.5); −0.0085 (1.1) Example number I-534: 1H-NMR(400.6 MHz, CDCl3): δ = 8.7454 (6.3); 8.7435 (6.3); 7.3294 (2.9): 7.3091 (3.5); 7.2616 (27.5); 7.2563 (0.9); 7.2476 (5.5); 7.2420 (1.8); 7.2308 (1.7); 7.2251 (6.2); 7.2167 (0.6); 7.1404 (2.3); 7.1398 (2.3); 7.1202 (1.9); 7.1195 (1.9); 6.8825 (0.6); 6.8741 (6.1); 6.8684 (1.8); 6.8572 (1.6); 6.8516 (5.4); 2.5444 (16.0); 1.5589 (2.9); 1.4106 (0.9); 1.3392 (0.9); −0.0002 (16.5); −0.0085 (0.6) Example number I-535: 1H-NMR(400.6 MHz, CDCl3): δ = 8.7633 (4.3); 8.7615 (4.4); 7.2971 (2.0); 7.2768 (2.6); 7.2616 (33.3); 7.1232 (1.7); 7.1027 (1.3); 6.9932 (1.3); 6.9711 (1.4); 6.9662 (1.4); 6.9442 (1.4); 6.5980 (1.0); 6.5909 (1.1); 6.5803 (1.0); 6.5732 (1.1); 6.4540 (0.8); 6.4455 (1.0); 6.4382 (0.7); 6.4319 (0.7); 6.4235 (0.9); 6.4162 (0.6); 3.8083 (16.0); 2.5435 (1.0); 2.5384 (11.3); 1.5561 (3.3); 1.4108 (6.4); 0.0080 (0.5); −0.0002 (19.9); −0.0085 (0.7) Example number I-537: 1H-NMR(400.6 MHz, CDCl3): δ = 8.4912 (0.7); 8.4119 (16.0); 7.2628 (9.4); 7.0353 (3.1); 6.9062 (2.2); 6.9001 (0.7); 6.8891 (0.9); 6.8861 (2.4); 6.8831 (3.0); 6.8801 (0.8); 6.8691 (0.8); 6.8629 (2.8); 6.7252 (2.9); 6.7190 (0.8); 6.7144 (3.0); 6.7082 (1.5); 6.7021 (2.1); 6.6973 (0.8); 6.6914 (2.1); 5.2987 (2.3); 2.4986 (14.8); 2.2058 (13.0); 2.2047 (12.0); −0.0002 (7.3) Example number I-548: 1H-NMR(400.6 MHz, CDCl3): δ = 7.9331 (3.9); 7.9276 (4.1); 7.4496 (2.2); 7.4440 (2.2); 7.4277 (2.2); 7.4222 (2.2); 7.2604 (14.1); 6.9365 (5.0); 6.9310 (1.3); 6.9196 (1.0); 6.9165 (2.5); 6.9136 (3.4); 6.9106 (1.0); 6.8995 (0.9); 6.8934 (3.2); 6.7787 (3.2); 6.7726 (0.9); 6.7679 (3.2); 6.7617 (1.5); 6.7557 (2.3); 6.7509 (0.8); 6.7450 (2.2); 2.4100 (16.0); 2.2027 (13.7); 2.2019 (13.6); −0.0002 (10.8) Example number I-570: 1H-NMR(400.6 MHz, CDCl3): δ = 8.5206 (0.6); 8.3379 (15.0); 7.2623 (12.7); 7.0224 (3.4); 6.9050 (2.3); 6.8989 (0.8); 6.8878 (1.0); 6.8848 (2.6); 6.8818 (3.3); 6.8788 (0.9); 6.8678 (0.9); 6.8617 (3.0); 6.7314 (3.1); 6.7253 (0.9); 6.7207 (3.2); 6.7144 (1.6); 6.7083 (2.2); 6.7036 (0.9); 6.6976 (2.2); 2.4905 (16.0); 2.2055 (14.2); 2.2044 (13.2); −0.0002 (9.9)

NMR Data of the End Products (Manual Evaluation)

Example number I-154: 1H-NMR (400.0 MHz, d6-DMSO): δ = 8.80 (s, 2H), 8.19-8.17 (m, 1H), 7.54-7.50 (m, 3H), 7.32-7.27 (m, 3H) Example number I-156: 1H-NMR (300.0 MHz, d6-DMSO): δ = 8.81 (s, 2H), 8.20-8.17 (m, 1H), 7.67-7.43 (m, 3H), 7.32-7.17 (m, 2H) Example number I-157: 1H-NMR (400.0 MHz, d6-DMSO): δ = 8.75 (s, 2H), 8.33-8.31 (m, 1H), 7.92-7.90 (m, 1H), 7.69-7.60 (m, 4H), 7.41-7.38 (m, 1H) Example number I-158: 1H-NMR (400.0 MHz, d6-DMSO): δ = 8.78 (s, 2H), 8.30-8.29 (m, 1H), 7.86-7.84 (m, 1H), 7.41-7.29 (m, 5H) Example number I-162: 1H-NMR (400.0 MHz, d6-DMSO): δ = 8.79 (s, 2H), 8.21-8.19 (m, 1H), 7.59-7.57 (m, 1H), 7.43-7.40 (m, 5H), 7.33-7.29 (m, 1H) Example number I-172: 1H-NMR (400.0 MHz, d6-DMSO): δ = 8.69 (d, 2H), 8.21-8.19 (m, 1H), 7.54-7.49 (m, 3H), 7.37-7.26 (m, 4H) Example number I-174: 1H-NMR (400.0 MHz, d6-DMSO): δ = 8.69 (d, 2H), 8.21-8.20 (m, 1H), 7.61-7.45 (m, 3H), 7.37-7.29 (m, 2H), 7.18-7.17 (m, 1H) Example number I-175: 1H-NMR (400.0 MHz, d6-DMSO): δ = 8.64 (d, 2H), 8.35 (dd, 1H), 7.91 (dd, 1H), 7.67-7.59 (m, 4H), 7.40 (dd, 1H), 7.32 (t, 1H) Example number I-176: 1H-NMR (400.0 MHz, d6-DMSO): δ = 8.67 (d, 2H), 8.32 (dd, 1H), 7.85 (dd, 1H), 7.40-7.29 (m, 6H) Example number I-180: 1H-NMR (400.0 MHz, d6-DMSO): δ = 8.69 (d, 2H), 8.22 (dd, 1H), 7.57 (dd, 1H), 7.42-7.30 (m, 7H) Example number I-210: 1H-NMR (400.0 MHz, d6-DMSO): δ = 8.58 (d, 2H), 8.26 (d, 1H), 7.39 (d, 1H), 7.29-7.23 (m, 2H), 7.17-7.11 (m, 1H), 6.99-6.94 (m, 1H), 2.50 (s, 3H) Example number I-212: 1H-NMR (400.0 MHz, d6-DMSO): δ = 8.61 (d, 2H), 8.33 (d, 1H), 7.44 (d, 1H), 7.30-7.20 (m, 3H), 7.10-7.02 (m, 2H), 2.43 (s, 3H) Example number I-216: 1H-NMR (400.0 MHz, d6-DMSO): δ = 8.62 (d, 2H), 8.30 (d, 1H), 7.41 (d, 1H), 7.29-7.24 (m, 3H), 7.16 (t, 1H), 7.09-7.07 (m, 2H), 2.40 (s, 3H) Example number I-591: 1H-NMR (400.0 MHz, CDCl3): δ = 8.38 (s, 2H), 7.79 (d, 1H), 7.43 (dd, 1H), 7.04 (s, 1H), 2.49 (s, 3H), 2.25 (s, 3H) Example number I-595: 1H-NMR (400.0 MHz, CDCl3): δ = 8.37 (s, 2H), 8.35 (s, 2H), 7.05 (s, 1H), 2.49 (s, 3H), 2.25 (s, 3H) Example number I-649: 1H-NMR (400.0 MHz, CDCl3): δ = 8.38 (s, 2H), 7.96 (d, 1H), 7.45 (dd, 1H), 6.95 (s, 1H), 2.40 (s, 3H), 2.25 (s, 3H)

The present invention further provides for the use of one or more compounds of the general formula (I) and/or salts thereof, as defined above, preferably in one of the embodiments identified as preferred or particularly preferred, in particular one or more compounds of the formulae (I-001) to (I-662) and/or salts thereof, in each case as defined above, as herbicide and/or plant growth regulator, preferably in crops of useful plants and/or ornamentals.

The present invention further provides a method for controlling harmful plants and/or for regulating the growth of plants, characterized in that an effective amount

    • of one or more compounds of the general formula (I) and/or salts thereof, as defined above, preferably in one of the embodiments identified as preferred or particularly preferred, in particular one or more compounds of the formulae (I-001) to (I-662) and/or salts thereof, in each case as defined above, or
    • of a composition according to the invention, as defined below,
    • is applied to the (harmful) plants, seeds of (harmful) plants, the soil in which or on which the (harmful) plants grow or the area under cultivation.

The present invention also provides a method for controlling unwanted plants, preferably in crops of useful plants, characterized in that an effective amount

    • of one or more compounds of the general formula (I) and/or salts thereof, as defined above, preferably in one of the embodiments identified as preferred or particularly preferred, in particular one or more compounds of the formulae (I-001) to (I-662) and/or salts thereof, in each case as defined above, or
    • of a composition according to the invention, as defined below,
    • is applied to unwanted plants (for example harmful plants such as mono- or dicotyledonous weeds or unwanted crop plants), the seed of the unwanted plants (i.e. plant seeds, for example grains, seeds or vegetative propagation organs such as tubers or shoot parts with buds), the soil in which or on which the unwanted plants grow (for example the soil of crop land or non-crop land) or the area under cultivation (i.e. the area on which the unwanted plants will grow).

The present invention also further provides methods for controlling for regulating the growth of plants, preferably of useful plants, characterized in that an effective amount

    • of one or more compounds of the general formula (I) and/or salts thereof, as defined above, preferably in one of the embodiments identified as preferred or particularly preferred, in particular one or more compounds of the formulae (I-001) to (I-662) and/or salts thereof, in each case as defined above, or
    • of a composition according to the invention, as defined below,
    • is applied to the plant, the seed of the plant (i.e. plant seeds, for example grains, seeds or vegetative propagation organs such as tubers or shoot parts with buds), the soil in which or on which the plants grow (for example the soil of crop land or non-crop land) or the area under cultivation (i.e. the area on which the plants will grow).

In this context, the compounds according to the invention or the compositions according to the invention can be applied for example by pre-sowing (if appropriate also by incorporation into the soil), pre-emergence and/or post-emergence processes. Specific examples of some representatives of the monocotyledonous and dicotyledonous weed flora which can be controlled by the compounds according to the invention are as follows, though there is no intention to restrict the enumeration to particular species.

In a method according to the invention for controlling harmful plants or for regulating the growth of plants, one or more compounds of the general formula (I) and/or salts thereof are preferably employed for controlling harmful plants or for regulating growth in crops of useful plants or ornamental plants, where in a preferred embodiment the useful plants or ornamental plants are transgenic plants.

The compounds of the general formula (I) according to the invention and/or their salts are suitable for controlling the following genera of monocotyledonous and dicotyledonous harmful plants:

Monocotyledonous harmful plants of the genera: Aegilops, Agropyron, Agrostis, Alopecurus, Apera, Avena, Brachiaria, Bromus, Cenchrus, Commelina, Cynodon, Cyperus, Dactyloctenium, Digitaria, Echinochloa, Eleocharis, Eleusine, Eragrostis, Eriochloa, Festuca, Fimbristylis, Heteranthera, Imperata, Ischaemum, Leptochloa, Lolium, Monochoria, Panicum, Paspalum, Phalaris, Phleum, Poa, Rottboellia, Sagittaria, Scirpus, Setaria, Sorghum.

Dicotyledonous harmful plants of the genera: Abutilon, Amaranthus, Ambrosia, Anoda, Anthemis, Aphanes, Artemisia, Atriplex, Bellis, Bidens, Capsella, Carduus, Cassia, Centaurea, Chenopodium, Cirsium, Convolvulus, Datura, Desmodium, Emex, Erysimum, Euphorbia, Galeopsis, Galinsoga, Galium, Hibiscus, Ipomoea, Kochia, Lamium, Lepidium, Lindernia, Matricaria, Mentha, Mercurialis, Mullugo, Myosotis, Papaver, Pharbitis, Plantago, Polygonum, Portulaca, Ranunculus, Raphanus, Rorippa, Rotala, Rumex, Salsola, Senecio, Sesbania, Sida, Sinapis, Solanum, Sonchus, Sphenoclea, Stellaria, Taraxacum, Thlaspi, Trifolium, Urtica, Veronica, Viola, Xanthium.

When the compounds of the general formula (I) according to the invention are applied to the soil surface before germination of the harmful plants (weed grasses and/or broad-leaved weeds) (pre-emergence method), either the seedlings of the weed grasses or broad-leaved weeds are prevented completely from emerging or they grow until they have reached the cotyledon stage, but then stop growing and eventually, after three to four weeks have elapsed, die completely.

If the active compounds of the general formula (I) are applied post-emergence to the green parts of the plants, growth stops after the treatment, and the harmful plants remain at the growth stage at the time of application, or they die completely after a certain time, so that in this manner competition by the weeds, which is harmful to the crop plants, is eliminated very early and in a sustained manner.

Although the compounds of the general formula (I) according to the invention display outstanding herbicidal activity against monocotyledonous and dicotyledonous weeds, crop plants of economically important crops, for example dicotyledonous crops of the genera Arachis, Beta, Brassica, Cucumis, Cucurbita, Helianthus, Daucus, Glycine, Gossypium, Ipomoea, Lactuca, Linum, Lycopersicon, Miscanthus, Nicotiana, Phaseolus, Pisum, Solanum, Vicia, or monocotyledonous crops of the genera Allium, Ananas, Asparagus, Avena, Hordeum, Oryza, Panicum, Saccharum, Secale, Sorghum, Triticale, Triticum, Zea, are damaged only to an insignificant extent, or not at all, depending on the structure of the respective compound according to the invention and its application rate. For these reasons, the present compounds are very suitable for selective control of unwanted plant growth in plant crops such as agriculturally useful plants or ornamental plants.

In addition, the compounds of the general formula (I) according to the invention (depending on their particular structure and the application rate deployed) have outstanding growth-regulating properties in crop plants. They intervene in the plants' own metabolism with regulatory effect, and can thus be used for the controlled influencing of plant constituents and to facilitate harvesting, for example by triggering desiccation and stunted growth. Furthermore, they are also suitable for the general control and inhibition of unwanted vegetative growth without killing the plants in the process. Inhibition of vegetative growth plays a major role for many mono- and dicotyledonous crops since, for example, this can reduce or completely prevent lodging.

By virtue of their herbicidal and plant growth regulatory properties, the active compounds of the general formula (I) can also be used to control harmful plants in crops of genetically modified plants or plants modified by conventional mutagenesis. In general, the transgenic plants are characterized by particular advantageous properties, for example by resistances to certain pesticides, in particular certain herbicides, resistances to plant diseases or pathogens of plant diseases, such as certain insects or microorganisms such as fungi, bacteria or viruses. Other specific characteristics relate, for example, to the harvested material with regard to quantity, quality, storability, composition and specific constituents. For instance, there are known transgenic plants with an elevated starch content or altered starch quality, or those with a different fatty acid composition in the harvested material.

It is preferred with a view to transgenic crops to use the compounds of the general formula (I) according to the invention and/or their salts in economically important transgenic crops of useful plants and ornamentals, for example of cereals such as wheat, barley, rye, oats, millet, rice and corn or else crops of sugar beet, cotton, soybean, oilseed rape, potato, tomato, peas and other vegetables.

It is preferable to employ the compounds of the general formula (I) according to the invention also as herbicides in crops of useful plants which are resistant, or have been made resistant by recombinant means, to the phytotoxic effects of the herbicides.

By virtue of their herbicidal and plant growth regulatory properties, the compounds of the general formula (I) according to the invention can also be used to control harmful plants in crops of genetically modified plants which are known or are yet to be developed. In general, the transgenic plants are characterized by particular advantageous properties, for example by resistances to certain pesticides, in particular certain herbicides, resistances to plant diseases or pathogens of plant diseases, such as certain insects or microorganisms such as fungi, bacteria or viruses. Other specific characteristics relate, for example, to the harvested material with regard to quantity, quality, storability, composition and specific constituents. For instance, there are known transgenic plants with an elevated starch content or altered starch quality, or those with a different fatty acid composition in the harvested material. Further special properties may be tolerance or resistance to abiotic stressors, for example heat, cold, drought, salinity and ultraviolet radiation.

Preference is given to the use of the compounds of the general formula (I) according to the invention or salts thereof in economically important transgenic crops of useful plants and ornamentals, for example of cereals such as wheat, barley, rye, oats, triticale, millet, rice, cassava and corn, or else crops of sugar beet, cotton, soybean, oilseed rape, potatoes, tomatoes, peas and other vegetables.

It is preferable to employ the compounds of the general formula (I) as herbicides in crops of useful plants which are resistant, or have been made resistant by recombinant means, to the phytotoxic effects of the herbicides.

Conventional ways of producing novel plants which have modified properties in comparison to existing plants consist, for example, in traditional cultivation methods and the generation of mutants.

Alternatively, novel plants with altered properties can be generated with the aid of recombinant methods.

A large number of molecular-biological techniques by means of which novel transgenic plants with modified properties can be generated are known to the person skilled in the art. For such genetic manipulations, nucleic acid molecules which allow mutagenesis or sequence alteration by recombination of DNA sequences can be introduced into plasmids. With the aid of standard methods, it is possible, for example, to undertake base exchanges, remove part sequences or add natural or synthetic sequences. To connect the DNA fragments to each other, adapters or linkers may be added to the fragments.

For example, the generation of plant cells with a reduced activity of a gene product can be achieved by expressing at least one corresponding antisense RNA, a sense RNA for achieving a cosuppression effect, or by expressing at least one suitably constructed ribozyme which specifically cleaves transcripts of the abovementioned gene product.

To this end, it is firstly possible to use DNA molecules which encompass the entire coding sequence of a gene product inclusive of any flanking sequences which may be present, and also DNA molecules which only encompass portions of the coding sequence, in which case it is necessary for these portions to be long enough to have an antisense effect in the cells. It is also possible to use DNA sequences which have a high degree of homology to the coding sequences of a gene product, but are not completely identical to them.

When expressing nucleic acid molecules in plants, the protein synthesized may be localized in any desired compartment of the plant cell. However, to achieve localization in a particular compartment, it is possible, for example, to join the coding region to DNA sequences which ensure localization in a particular compartment. Such sequences are known to those skilled in the art (see, for example, Braun et al., EMBO J. 11 (1992), 3219-3227). The nucleic acid molecules can also be expressed in the organelles of the plant cells.

The transgenic plant cells can be regenerated by known techniques to give rise to entire plants. In principle, the transgenic plants may be plants of any desired plant species, i.e. not only monocotyledonous but also dicotyledonous plants.

Thus, transgenic plants can be obtained whose properties are altered by overexpression, suppression or inhibition of homologous (=natural) genes or gene sequences or expression of heterologous (=foreign) genes or gene sequences.

It is preferred to employ the compounds of the general formula (I) according to the invention in transgenic crops which are resistant to growth regulators such as, for example, dicamba, or to herbicides which inhibit essential plant enzymes, for example acetolactate synthases (ALS), EPSP synthases, glutamine synthases (GS) or hydroxyphenylpyruvate dioxygenases (HPPD), or to herbicides from the group of the sulfonylureas, glyphosate, glufosinate or benzoylisoxazoles and analogous active compounds.

When the compounds of the general formula (I) according to the invention are employed in transgenic crops, not only do the effects toward harmful plants observed in other crops occur, but frequently also effects which are specific to application in the particular transgenic crop, for example an altered or specifically widened spectrum of weeds which can be controlled, altered application rates which can be used for the application, preferably good combinability with the herbicides to which the transgenic crop is resistant, and influencing of growth and yield of the transgenic crop plants.

The invention therefore also relates to the use of the compounds of the general formula (I) according to the invention and/or their salts as herbicides for controlling harmful plants in crops of useful plants or ornamentals, optionally in transgenic crop plants.

Preference is given to the use of compounds of the general formula (I) in cereals, here preferably corn, wheat, barley, rye, oats, millet or rice, by the pre- or post-emergence method.

Preference is also given to the use of compounds of the general formula (I) in soybean by the pre-emergence or post-emergence method.

The use of inventive compounds of the formula (I) for the control of harmful plants or for growth regulation of plants also includes the case in which a compound of the general formula (I) or its salt is not formed from a precursor substance (“prodrug”) until after application on the plant, in the plant or in the soil.

The invention also provides the use of one or more compounds of the general formula (I) or salts thereof or of a composition according to the invention (as defined below) (in a method) for controlling harmful plants or for regulating the growth of plants which comprises applying an effective amount of one or more compounds of the general formula (I) or salts thereof onto the plants (harmful plants, if appropriate together with the useful plants), plant seeds, the soil in which or on which the plants grow or the area under cultivation.

The invention also provides a herbicidal and/or plant growth-regulating composition, characterized in that the composition comprises

(a) one or more compounds of the general formula (I) and/or salts thereof, as defined above, preferably in one of the embodiments identified as preferred or particularly preferred, in particular one or more compounds of the formulae

(I-001) to (I-662) and/or salts thereof, in each case as defined above,

and

(b) one or more further substances selected from groups (i) and/or (ii):

    • (i) one or more further agrochemically active substances, preferably selected from the group consisting of insecticides, acaricides, nematicides, further herbicides (i.e. those not conforming to the general formula (I) defined above), fungicides, safeners, fertilizers and/or further growth regulators,
    • (ii) one or more formulation auxiliaries customary in crop protection.

Here, the further agrochemically active substances of component (i) of a composition according to the invention are preferably selected from the group of substances mentioned in “The Pesticide Manual”, 16th edition, The British Crop Protection Council and the Royal Soc. of Chemistry, 2012.

A herbicidal or plant growth-regulating composition according to the invention comprises preferably one, two, three or more formulation auxiliaries (ii) customary in crop protection selected from the group consisting of surfactants, emulsifiers, dispersants, film-formers, thickeners, inorganic salts, dusting agents, carriers solid at 25° C. and 1013 mbar, preferably adsorptive granulated inert materials, wetting agents, antioxidants, stabilizers, buffer substances, antifoam agents, water, organic solvents, preferably organic solvents miscible with water in any ratio at 25° C. and 1013 mbar.

The compounds of the general formula (I) according to the invention can be used in the form of wettable powders, emulsifiable concentrates, sprayable solutions, dusting products or granules in the customary formulations. The invention therefore also provides herbicidal and plant growth-regulating compositions which comprise compounds of the general formula (I) and/or salts thereof.

The compounds of the general formula (I) according to the invention and/or salts thereof can be formulated in various ways according to which biological and/or physicochemical parameters are specified. Possible formulations include, for example: wettable powders (WP), water-soluble powders (SP), water-soluble concentrates, emulsifiable concentrates (EC), emulsions (EW), such as oil-in-water and water-in-oil emulsions, sprayable solutions, suspension concentrates (SC), dispersions based on oil or water, oil-miscible solutions, capsule suspensions (CS), dusting products (DP), dressings, granules for scattering and soil application, granules (GR) in the form of microgranules, spray granules, absorption and adsorption granules, water-dispersible granules (WG), water-soluble granules (SG), ULV formulations, microcapsules and waxes.

These individual formulation types and the formulation assistants, such as inert materials, surfactants, solvents and further additives, are known to the person skilled in the art and are described, for example, in: Watkins, “Handbook of Insecticide Dust Diluents and Carriers”, 2nd Ed., Darland Books, Caldwell N. J.; H. v. Olphen, “Introduction to Clay Colloid Chemistry”, 2nd ed., J. Wiley & Sons, N.Y.; C. Marsden, “Solvents Guide”, 2nd ed., Interscience, N.Y. 1963; McCutcheon's “Detergents and Emulsifiers Annual”, MC Publ. Corp., Ridgewood N.J.; Sisley and Wood, “Encyclopedia of Surface Active Agents”, Chem. Publ. Co. Inc., N.Y. 1964; Schönfeldt, “Grenzflächenaktive Äthylenoxidaddukte” [Interface-active Ethylene Oxide Adducts], Wiss. Verlagsgesellschaft, Stuttgart 1976; Winnacker-Küchler, “Chemische Technologie” [Chemical Technology], volume 7, C. Hanser Verlag Munich, 4th Ed. 1986.

Wettable powders are preparations which can be dispersed uniformly in water and, in addition to the active compound, apart from a diluent or inert substance, also comprise surfactants of the ionic and/or nonionic type (wetting agents, dispersants), for example polyoxyethylated alkylphenols, polyoxyethylated fatty alcohols, polyoxyethylated fatty amines, fatty alcohol polyglycol ether sulfates, alkanesulfonates, alkylbenzenesulfonates, sodium lignosulfonate, sodium 2,2′-dinaphthylmethane-6,6′-disulfonate, sodium dibutylnaphthalenesulfonate or else sodium oleoylmethyltaurate. To produce the wettable powders, the herbicidally active compounds are finely ground, for example in customary apparatuses such as hammer mills, blower mills and air-jet mills, and simultaneously or subsequently mixed with the formulation auxiliaries.

Emulsifiable concentrates are produced by dissolving the active compound in an organic solvent, for example butanol, cyclohexanone, dimethylformamide, xylene, or else relatively high-boiling aromatics or hydrocarbons or mixtures of the organic solvents, with addition of one or more ionic and/or nonionic surfactants (emulsifiers). Examples of emulsifiers which may be used are: calcium alkylarylsulfonate salts, for example calcium dodecylbenzenesulfonate, or nonionic emulsifiers such as fatty acid polyglycol esters, alkylaryl polyglycol ethers, fatty alcohol polyglycol ethers, propylene oxide-ethylene oxide condensation products, alkyl polyethers, sorbitan esters, for example sorbitan fatty acid esters, or polyoxyethylene sorbitan esters, for example polyoxyethylene sorbitan fatty acid esters.

Dusting products are obtained by grinding the active compound with finely distributed solids, for example talc, natural clays, such as kaolin, bentonite and pyrophyllite, or diatomaceous earth.

Suspension concentrates may be water- or oil-based. They may be prepared, for example, by wet-grinding by means of commercial bead mills and optional addition of surfactants as have, for example, already been listed above for the other formulation types.

Emulsions, for example oil-in-water emulsions (EW), can be produced, for example, by means of stirrers, colloid mills and/or static mixers using aqueous organic solvents and optionally surfactants as already listed above, for example, for the other formulation types.

Granules can be prepared either by spraying the active compound onto granular inert material capable of adsorption or by applying active compound concentrates to the surface of carrier substances, such as sand, kaolinites or granular inert material, by means of adhesives, for example polyvinyl alcohol, sodium polyacrylate or mineral oils. Suitable active compounds can also be granulated in the manner customary for the production of fertilizer granules—if desired as a mixture with fertilizers.

Water-dispersible granules are produced generally by the customary processes such as spray-drying, fluidized-bed granulation, pan granulation, mixing with high-speed mixers and extrusion without solid inert material.

For the production of pan, fluidized-bed, extruder and spray granules, see e.g. processes in “Spray-Drying Handbook” 3rd Ed. 1979, G. Goodwin Ltd., London; J. E. Browning, “Agglomeration”, Chemical and Engineering 1967, pages 147 ff; “Perry's Chemical Engineer's Handbook”, 5th Ed., McGraw Hill, New York 1973, p. 8-57.

For further details regarding the formulation of crop protection compositions, see, for example, G. C. Klingman, “Weed Control as a Science”, John Wiley and Sons, Inc., New York, 1961, pages 81-96 and J. D. Freyer, S. A. Evans, “Weed Control Handbook”, 5th Ed., Blackwell Scientific Publications, Oxford, 1968, pages 101-103.

The agrochemical preparations, preferably herbicidal or plant growth-regulating compositions, of the present invention preferably comprise a total amount of from 0.1 to 99% by weight, preferably 0.5 to 95% by weight, particularly preferably 1 to 90% by weight, especially preferably 2 to 80% by weight, of active compounds of the general formula (I) and their salts.

In wettable powders, the active compound concentration is, for example, about 10 to 90% by weight, the remainder to 100% by weight consisting of customary formulation constituents. In emulsifiable concentrates, the active compound concentration may be about 1% to 90% and preferably 5% to 80% by weight. Formulations in the form of dusts comprise 1% to 30% by weight of active compound, preferably usually 5% to 20% by weight of active compound; sprayable solutions contain about 0.05% to 80% by weight, preferably 2% to 50% by weight of active compound. In the case of water-dispersible granules, the active compound content depends partially on whether the active compound is in liquid or solid form and on which granulation auxiliaries, fillers, etc., are used. In the water-dispersible granules, the content of active compound is, for example, between 1 and 95% by weight, preferably between 10 and 80% by weight.

In addition, the active compound formulations mentioned optionally comprise the respective customary stickers, wetters, dispersants, emulsifiers, penetrants, preservatives, antifreeze agents and solvents, fillers, carriers and dyes, defoamers, evaporation inhibitors and agents which influence the pH and the viscosity. Examples of formulation auxiliaries are described inter alia in “Chemistry and Technology of Agrochemical Formulations”, ed. D. A. Knowles, Kluwer Academic Publishers (1998).

The compounds of the general formula (I) according to the invention or salts thereof can be used as such or in the form of their preparations (formulations) in a combination with other pesticidally active substances, for example insecticides, acaricides, nematicides, herbicides, fungicides, safeners, fertilizers and/or growth regulators, for example in the form of a finished formulation or of a tank mix. The combination formulations can be prepared on the basis of the abovementioned formulations, while taking account of the physical properties and stabilities of the active compounds to be combined.

Active compounds which can be employed in combination with the compounds of the general formula (I) according to the invention in mixture formulations or in a tank mix are, for example, known active compounds based on inhibition of, for example, acetolactate synthase, acetyl-CoA carboxylase, cellulose synthase, enolpyruvylshikimate-3-phosphate synthase, glutamine synthetase, p-hydroxyphenylpyruvate dioxygenase, phytoene desaturase, photosystem I, photosystem II, protoporphyrinogen oxidase, as described, for example, in Weed Research 26 (1986) 441-445 or “The Pesticide Manual”, 16th edition, The British Crop Protection Council and the Royal Soc. of Chemistry, 2012 and literature cited therein.

Of particular interest is the selective control of harmful plants in crops of useful plants and ornamentals. Although the compounds of the general formula (I) according to the invention have already demonstrated very good to adequate selectivity in a large number of crops, in principle, in some crops and in particular also in the case of mixtures with other, less selective herbicides, phytotoxicities on the crop plants may occur. In this connection, combinations of compounds (I) according to the invention that are of particular interest are those which comprise the compounds of the general formula (I) or their combinations with other herbicides or pesticides and safeners. The safeners, which are used in an antidotically effective amount, reduce the phytotoxic side effects of the herbicides/pesticides employed, for example in economically important crops, such as cereals (wheat, barley, rye, corn, rice, millet), sugarbeet, sugarcane, oilseed rape, cotton and soybeans, preferably cereals.

The weight ratios of herbicide (mixture) to safener depend generally on the herbicide application rate and the efficacy of the safener in question and may vary within wide limits, for example in the range from 200:1 to 1:200, preferably 100:1 to 1:100, in particular 20:1 to 1:20. Analogously to the compounds of the general formula (I) or mixtures thereof, the safeners can be formulated with further herbicides/pesticides and be provided and employed as a finished formulation or tank mix with the herbicides.

For application, the herbicide or herbicide/safener formulations present in commercial form are, if appropriate, diluted in a customary manner, for example in the case of wettable powders, emulsifiable concentrates, dispersions and water-dispersible granules with water. Dust-type preparations, granules for soil application or granules for scattering and sprayable solutions are not normally diluted further with other inert substances prior to application.

The application rate of the compounds of the general formula (I) and/or their salts is affected to a certain extent by external conditions such as temperature, humidity, etc. Here, the application rate may vary within wide limits. For the application as a herbicide for controlling harmful plants, the total amount of compounds of the general formula (I) and their salts is preferably in the range from 0.001 to 10.0 kg/ha, with preference in the range from 0.005 to 5 kg/ha, more preferably in the range from 0.01 to 1.5 kg/ha, particularly preferably in the range from 0.05 to 1 kg/ha. This applies both to the pre-emergence and the post-emergence application.

When the compounds of the general formula (I) according to the invention and/or their salts are used as plant growth regulator, for example as culm stabilizer for crop plants like those mentioned above, preferably cereal plants, such as wheat, barley, rye, triticale, millet, rice or corn, the total application rate is preferably in the range of from 0.001 to 2 kg/ha, preferably in the range of from 0.005 to 1 kg/ha, in particular in the range of from 10 to 500 g/ha, very particularly preferably in the range of from 20 to 250 g/ha. This applies both to the pre-emergence and the post-emergence application.

The application as culm stabilizer may take place at various stages of the growth of the plants. Preferred is, for example, the application after the tittering phase, at the beginning of the longitudinal growth.

As an alternative, application as plant growth regulator is also possible by treating the seed, which includes various techniques for dressing and coating seed. Here, the application rate depends on the particular techniques and can be determined in preliminary tests.

Active compounds which can be employed in combination with the compounds of the general formula (I) according to the invention in compositions according to the invention (for example in mixed formulations or in the tank mix) are, for example, known active compounds which are based on the inhibition of, for example, acetolactate synthase, acetyl-CoA carboxylase, cellulose synthase, enolpyruvylshikimate-3-phosphate synthase, glutamine synthetase, p-hydroxyphenylpyruvate dioxygenase, phytoene desaturase, photosystem I, photosystem II or protoporphyrinogen oxidase, as are described in, for example, Weed Research 26 (1986) 441-445 or “The Pesticide Manual”, 16th edition, The British Crop Protection Council and the Royal Soc. of Chemistry, 2012 and the literature cited therein. Known herbicides or plant growth regulators which can be combined with the compounds according to the invention are, for example, the following, where said active compounds are designated either with their “common name” in accordance with the International Organization for Standardization (ISO) or with the chemical name or with the code number. They always encompass all of the application forms such as, for example, acids, salts, esters and also all isomeric forms such as stereoisomers and optical isomers, even if they are not explicitly mentioned.

Examples of such herbicidal mixing partners are:

acetochlor, acifluorfen, acifluorfen-sodium, aclonifen, alachlor, allidochlor, alloxydim, alloxydim-sodium, ametryn, amicarbazone, amidochlor, amidosulfuron, 4-amino-3-chloro-6-(4-chloro-2-fluoro-3-methylphenyl)-5-fluoropyridine-2-carboxylic acid, aminocyclopyrachlor, aminocyclopyrachlor-potassium, aminocyclopyrachlor-methyl, aminopyralid, amitrole, ammonium sulfamate, anilofos, asulam, atrazine, azafenidin, azimsulfuron, beflubutamid, benazolin, benazolin-ethyl, benfluralin, benfuresate, bensulfuron, bensulfuron-methyl, bensulide, bentazone, benzobicyclon, benzofenap, bicyclopyron, bifenox, bilanafos, bilanafos-sodium, bispyribac, bispyribac-sodium, bromacil, bromobutide, bromofenoxim, bromoxynil, bromoxynil-butyrate, -potassium, -heptanoate and -octanoate, busoxinone, butachlor, butafenacil, butamifos, butenachlor, butralin, butroxydim, butylate, cafenstrole, carbetamide, carfentrazone, carfentrazone-ethyl, chloramben, chlorbromuron, chlorfenac, chlorfenac-sodium, chlorfenprop, chlorflurenol, chlorflurenol-methyl, chloridazon, chlorimuron, chlorimuron-ethyl, chlorophthalim, chlorotoluron, chlorthal-dimethyl, chlorsulfuron, cinidon, cinidon-ethyl, cinmethylin, cinosulfuron, clacyfos, clethodim, clodinafop, clodinafop-propargyl, clomazone, clomeprop, clopyralid, cloransulam, cloransulam-methyl, cumyluron, cyanamide, cyanazine, cycloate, cyclopyrimorate, cyclosulfamuron, cycloxydim, cyhalofop, cyhalofop-butyl, cyprazine, 2,4-D, 2,4-D-butotyl, -butyl, -dimethylammonium, -diolamin, -ethyl, 2-ethylhexyl, -isobutyl, -isooctyl, -isopropylammonium, -potassium, -triisopropanolammonium and -trolamine, 2,4-DB, 2,4-DB-butyl, -dimethylammonium, isooctyl, -potassium and -sodium, daimuron (dymron), dalapon, dazomet, n-decanol, desmedipham, detosyl-pyrazolate (DTP), dicamba, dichlobenil, 2-(2,4-dichlorobenzyl)-4,4-dimethyl-1,2-oxazolidin-3-one, 2-(2,5-dichlorobenzyl)-4,4-dimethyl-1,2-oxazolidin-3-one, dichlorprop, dichlorprop-P, diclofop, diclofop-methyl, diclofop-P-methyl, diclosulam, difenzoquat, diflufenican, diflufenzopyr, diflufenzopyr-sodium, dimefuron, dimepiperate, dimethachlor, dimethametryn, dimethenamid, dimethenamid-P, dimetrasulfuron, dinitramine, dinoterb, diphenamid, diquat, diquat-dibromid, dithiopyr, diuron, DNOC, endothal, EPTC, esprocarb, ethalfluralin, ethametsulfuron, ethametsulfuron-methyl, ethiozin, ethofumesate, ethoxyfen, ethoxyfen-ethyl, ethoxysulfuron, etobenzanid, F-9600, F-5231, i.e. N-[2-chloro-4-fluoro-5-[4-(3-fluoropropyl)-4,5-dihydro-5-oxo-1H-tetrazol-1-yl]phenyl]ethanesulfonamide, F-7967, i.e. 3-[7-chloro-5-fluoro-2-(trifluoromethyl)-1H-benzimidazol-4-yl]-1-methyl-6-(trifluoromethyl)pyrimidine-2,4(1H,3H)-dione, fenoxaprop, fenoxaprop-P, fenoxaprop-ethyl, fenoxaprop-P-ethyl, fenoxasulfone, fenquinotrione, fentrazamide, flamprop, flamprop-M-isopropyl, flamprop-M-methyl, flazasulfuron, florasulam, fluazifop, fluazifop-P, fluazifop-butyl, fluazifop-P-butyl, flucarbazone, flucarbazone-sodium, flucetosulfuron, fluchloralin, flufenacet, flufenpyr, flufenpyr-ethyl, flumetsulam, flumiclorac, flumiclorac-pentyl, flumioxazin, fluometuron, flurenol, flurenol-butyl, -dimethylammonium and -methyl, fluoroglycofen, fluoroglycofen-ethyl, flupropanate, flupyrsulfuron, flupyrsulfuron-methyl-sodium, fluridone, flurochloridone, fluroxypyr, fluroxypyr-meptyl, flurtamone, fluthiacet, fluthiacet-methyl, fomesafen, fomesafen-sodium, foramsulfuron, fosamine, glufosinate, glufosinate-ammonium, glufosinate-P-sodium, glufosinate-P-ammonium, glufosinate-P-sodium, glyphosate, glyphosate-ammonium, -isopropylammonium, -diammonium, -dimethylammonium, -potassium, -sodium and -trimesium, H-9201, i.e. 0-(2,4-dimethyl-6-nitrophenyl) O-ethyl isopropylphosphoramidothioate, halauxifen, halauxifen-methyl, halosafen, halosulfuron, halosulfuron-methyl, haloxyfop, haloxyfop-P, haloxyfop-ethoxyethyl, haloxyfop-P-ethoxyethyl, haloxyfop-methyl, haloxyfop-P-methyl, hexazinone, HW-02, i.e. 1-(dimethoxyphosphoryl)ethyl (2,4-dichlorophenoxy)acetat, imazamethabenz, imazamethabenz-methyl, imazamox, imazamox-ammonium, imazapic, imazapic-ammonium, imazapyr, imazapyr-isopropylammonium, imazaquin, imazaquin-ammonium, imazethapyr, imazethapyr-immonium, imazosulfuron, indanofan, indaziflam, iodosulfuron, iodosulfuron-methyl-sodium, ioxynil, ioxynil-octanoate, -potassium and sodium, ipfencarbazone, isoproturon, isouron, isoxaben, isoxaflutole, karbutilate, KUH-043, i.e. 3-({[5-(difluoromethyl)-1-methyl-3-(trifluoromethyl)-1H-pyrazol-4-yl]methyl}sulfonyl)-5,5-dimethyl-4,5-dihydro-1,2-oxazole, ketospiradox, lactofen, lenacil, linuron, MCPA, MCPA-butotyl, -dimethylammonium, -2-ethylhexyl, -isopropylammonium, -potassium and -sodium, MCPB, MCPB-methyl, -ethyl and -sodium, mecoprop, mecoprop-sodium, and -butotyl, mecoprop-P, mecoprop-P-butotyl, -dimethylammonium, -2-ethylhexyl and -potassium, mefenacet, mefluidide, mesosulfuron, mesosulfuron-methyl, mesotrione, methabenzthiazuron, metam, metamifop, metamitron, metazachlor, metazosulfuron, methabenzthiazuron, methiopyrsulfuron, methiozolin, methyl isothiocyanate, metobromuron, metolachlor, S-metolachlor, metosulam, metoxuron, metribuzin, metsulfuron, metsulfuron-methyl, molinate, monolinuron, monosulfuron, monosulfuron-ester, MT-5950, i.e. N-[3-chloro-4-(1-methylethyl)phenyl]-2-methylpentanamide, NGGC-011, napropamide, NC-310, i.e. 4-(2,4-dichlorobenzoyl)-1-methyl-5-benzyloxypyrazole, neburon, nicosulfuron, nonanoic acid (pelargonic acid), norflurazon, oleic acid (fatty acids), orbencarb, orthosulfamuron, oryzalin, oxadiargyl, oxadiazon, oxasulfuron, oxaziclomefon, oxyfluorfen, paraquat, paraquat dichloride, pebulate, pendimethalin, penoxsulam, pentachlorophenol, pentoxazone, pethoxamid, petroleum oils, phenmedipham, picloram, picolinafen, pinoxaden, piperophos, pretilachlor, primisulfuron, primisulfuron-methyl, prodiamine, profoxydim, prometon, prometryn, propachlor, propanil, propaquizafop, propazine, propham, propisochlor, propoxycarbazone, propoxycarbazone-sodium, propyrisulfuron, propyzamide, prosulfocarb, prosulfuron, pyraclonil, pyraflufen, pyraflufen-ethyl, pyrasulfotole, pyrazolynate (pyrazolate), pyrazosulfuron, pyrazosulfuron-ethyl, pyrazoxyfen, pyribambenz, pyribambenz-isopropyl, pyribambenz-propyl, pyribenzoxim, pyributicarb, pyridafol, pyridate, pyriftalid, pyriminobac, pyriminobac-methyl, pyrimisulfan, pyrithiobac, pyrithiobac-sodium, pyroxasulfone, pyroxsulam, quinclorac, quinmerac, quinoclamine, quizalofop, quizalofop-ethyl, quizalofop-P, quizalofop-P-ethyl, quizalofop-P-tefuryl, rimsulfuron, saflufenacil, sethoxydim, siduron, simazine, simetryn, SL-261, sulcotrion, sulfentrazone, sulfometuron, sulfometuron-methyl, sulfosulfuron, SYN-523, SYP-249, i.e. 1-ethoxy-3-methyl-1-oxobut-3-en-2-yl5-[2-chlor-4-(trifluoromethyl)phenoxy]-2-nitrobenzoate, SYP-300, i.e. 1-[7-fluoro-3-oxo-4-(prop-2-yn-1-yl)-3,4-dihydro-2H-1,4-benzoxazin-6-yl]-3-propyl-2-thioxoimidazolidine-4,5-dione, 2,3,6-TBA, TCA (trifluoroacetic acid), TCA-sodium, tebuthiuron, tefuryltrione, tembotrione, tepraloxydim, terbacil, terbucarb, terbumeton, terbuthylazin, terbutryn, thenylchlor, thiazopyr, thiencarbazone, thiencarbazone-methyl, thifensulfuron, thifensulfuron-methyl, thiobencarb, tiafenacil, tolpyralate, topramezone, tralkoxydim, triafamone, tri-allate, triasulfuron, triaziflam, tribenuron, tribenuron-methyl, triclopyr, trietazine, trifloxysulfuron, trifloxysulfuron-sodium, trifludimoxazin, trifluralin, triflusulfuron, triflusulfuron-methyl, tritosulfuron, urea sulfate, vernolate, XDE-848, ZJ-0862, i.e. 3,4-dichloro-N-{2-[(4,6-dimethoxypyrimidin-2-yl)oxy]benzyl}aniline, and the following compounds

Examples of plant growth regulators as possible mixing partners are:

acibenzolar, acibenzolar-S-methyl, 5-aminolevulinic acid, ancymidol, 6-benzylaminopurine, brassinolide, catechol, chlormequat chloride, cloprop, cyclanilide, 3-(cycloprop-1-enyl)propionic acid, daminozide, dazomet, n-decanol, dikegulac, dikegulac-sodium, endothal, endothal-dipotassium, -disodium, and mono(N,N-dimethylalkylammonium), ethephon, flumetralin, flurenol, flurenol-butyl, flurprimidol, forchlorfenuron, gibberellic acid, inabenfide, indole-3-acetic acid (IAA), 4-indol-3-ylbutyric acid, isoprothiolane, probenazole, jasmonic acid, jasmonic acid methyl ester, maleic hydrazide, mepiquat chloride, 1-methylcyclopropene, 2-(1-naphthyl)acetamide, 1-naphthylacetic acid, 2-naphthyloxyacetic acid, nitrophenolate mixture, 4-oxo-4[(2-phenylethyl)amino]butyric acid, paclobutrazole, N-phenylphthalamic acid, prohexadione, prohexadione-calcium, prohydrojasmone, salicylic acid, strigolactone, tecnazene, thidiazuron, triacontanol, trinexapac, trinexapac-ethyl, tsitodef, uniconazole, uniconazole-P.

Useful combination partners for the compounds of the general formula (I) according to the invention also include, for example, the following safeners:

    • S1) Compounds from the group of heterocyclic carboxylic acid derivatives:
    • S1a) Compounds of the dichlorophenylpyrazoline-3-carboxylic acid type (S1a), preferably compounds such as
    • 1-(2,4-dichlorophenyl)-5-(ethoxycarbonyl)-5-methyl-2-pyrazoline-3-carboxylic acid, ethyl 1-(2,4-dichlorophenyl)-5-(ethoxycarbonyl)-5-methyl-2-pyrazoline-3-carboxylate (S1-1) (“mefenpyr-diethyl”), and related compounds as described in WO-A-91/07874;
    • S1b) Derivatives of dichlorophenylpyrazolecarboxylic acid (S1b), preferably compounds such as ethyl 1-(2,4-dichlorophenyl)-5-methylpyrazole-3-carboxylate (S1-2), ethyl 1-(2,4-dichlorophenyl)-5-isopropylpyrazole-3-carboxylate (S1-3), ethyl 1-(2,4-dichlorophenyl)-5-(1,1-dimethylethyl)pyrazole-3-carboxylate (S1-4) and related compounds as described in EP-A-333131 and EP-A-269806;
    • S1c) Derivatives of 1,5-diphenylpyrazole-3-carboxylic acid (S1c), preferably compounds such as ethyl 1-(2,4-dichlorophenyl)-5-phenylpyrazole-3-carboxylate (S1-5), methyl 1-(2-chlorophenyl)-5-phenylpyrazole-3-carboxylate (S1-6) and related compounds as described, for example, in EP-A-268554;
    • S1d) Compounds of the triazolecarboxylic acid type (S1d), preferably compounds such as fenchlorazole(-ethyl ester), i.e. ethyl 1-(2,4-dichlorophenyl)-5-trichloromethyl-(1H)-1,2,4-triazole-3-carboxylate (S1-7), and related compounds, as described in EP-A-174562 and EP-A-346620;
    • S1e) Compounds of the 5-benzyl- or 5-phenyl-2-isoxazoline-3-carboxylic acid or of the 5,5-diphenyl-2-isoxazoline-3-carboxylic acid type (SP), preferably compounds such as ethyl 5-(2,4-dichlorobenzyl)-2-isoxazoline-3-carboxylate (S1-8) or ethyl 5-phenyl-2-isoxazoline-3-carboxylate (S1-9) and related compounds as described in WO-A-91/08202, or 5,5-diphenyl-2-isoxazolinecarboxylic acid (S1-10) or ethyl 5,5-diphenyl-2-isoxazoline-3-carboxylate (S1-11) (“isoxadifen-ethyl”) or n-propyl 5,5-diphenyl-2-isoxazoline-3-carboxylate (S1-12) or ethyl 5-(4-fluorophenyl)-5-phenyl-2-isoxazoline-3-carboxylate (S1-13) as described in patent application WO-A-95/07897.
    • S2) Compounds from the group of the 8-quinolinoxy derivatives (S2):
    • S2a) Compounds of the 8-quinolinoxyacetic acid type (S2a), preferably 1-methylhexyl (5-chloro-8-quinolinoxy)acetate (“cloquintocet-mexyl”) (S2-1), 1,3-dimethylbut-1-yl (5-chloro-8-quinolinoxy)acetate (S2-2), 4-allyloxybutyl (5-chloro-8-quinolinoxy)acetate (S2-3), 1-allyloxyprop-2-yl (5-chloro-8-quinolinoxy)acetate (S2-4), ethyl (5-chloro-8-quinolinoxy)acetate (S2-5),
    • methyl (5-chloro-8-quinolinoxy)acetate (S2-6),
    • allyl (5-chloro-8-quinolinoxy)acetate (S2-7), 2-(2-propylideneiminoxy)-1-ethyl (5-chloro-8-quinolinoxy)acetate (S2-8), 2-oxoprop-1-yl (5-chloro-8-quinolinoxy)acetate (S2-9) and related compounds, as described in EP-A-86750, EP-A-94349 and EP-A-191736 or EP-A-0 492 366, and also (5-chloro-8-quinolinoxy)acetic acid (S2-10), hydrates and salts thereof, for example the lithium, sodium, potassium, calcium, magnesium, aluminum, iron, ammonium, quaternary ammonium, sulfonium or phosphonium salts thereof, as described in WO-A-2002/34048;
    • S2b) Compounds of the (5-chloro-8-quinolinoxy)malonic acid type (S2b), preferably compounds such as diethyl (5-chloro-8-quinolinoxy)malonate, diallyl (5-chloro-8-quinolinoxy)malonate, methyl ethyl (5-chloro-8-quinolinoxy)malonate and related compounds, as described in EP-A-0 582 198.
    • S3) Active compounds of the dichloroacetamide type (S3), which are frequently used as pre-emergence safeners (soil-acting safeners), for example
    • “dichlormid” (N,N-diallyl-2,2-dichloroacetamide) (S3-1),
    • “R-29148” (3-dichloroacetyl-2,2,5-trimethyl-1,3-oxazolidine) from Stauffer (S3-2),
    • “R-28725” (3-dichloroacetyl-2,2-dimethyl-1,3-oxazolidine) from Stauffer (S3-3),
    • “benoxacor” (4-dichloroacetyl-3,4-dihydro-3-methyl-2H-1,4-benzoxazine) (S3-4),
    • “PPG-1292” (N-allyl-N-[(1,3-dioxolan-2-yl)methyl]dichloroacetamide) from PPG Industries (S3-5),
    • “DKA-24” (N-allyl-N-[(allylaminocarbonyl)methyl]dichloroacetamide) from Sagro-Chem (53-6),
    • “AD-67” or “MON 4660” (3-dichloroacetyl-1-oxa-3-azaspiro[4.5]decane) from Nitrokemia or Monsanto (53-7),
    • “TI-35” (1-dichloroacetylazepane) from TRI-Chemical RT (53-8),
    • “diclonon” (dicyclonon) or “BAS145138” or “LAB145138” (53-9)
    • ((RS)-1-dichloroacetyl-3,3,8a-trimethylperhydropyrrolo[1,2-a]pyrimidin-6-one) from BASF,
    • “furilazole” or “MON 13900” ((RS)-3-dichloroacetyl-5-(2-furyl)-2,2-dimethyloxazolidine) (53-10), and the (R) isomer thereof (S3-11).
    • S4) Compounds from the class of the acylsulfonamides (S4):
    • S4a) N-Acylsulfonamides of the formula (S4a) and salts thereof, as described in WO-A-97/45016,

    • in which
    • RA1 represents (C1-C6)-alkyl, (C3-C6)-cycloalkyl, where the 2 latter radicals are substituted by vA substituents from the group of halogen, (C1-C4)-alkoxy, (C1-C6)-haloalkoxy and (C1-C4)-alkylthio and, in the case of cyclic radicals, also by (C1-C4)-alkyl and (C1-C4)-haloalkyl;
    • RA2 represents halogen, (C1-C4)-alkyl, (C1-C4)-alkoxy, CF3;
    • mA represents 1 or 2;
    • vA represents 0, 1, 2 or 3;
    • S4b) Compounds of the 4-(benzoylsulfamoyl)benzamide type of the formula (S4b) and salts thereof, as described in WO-A-99/16744,

    • in which
    • RB1, RB2 independently of one another represent hydrogen, (C1-C6)-alkyl, (C3-C6)-cycloalkyl, (C3-C6)-alkenyl, (C3-C6)-alkynyl,
    • RB3 represents halogen, (C1-C4)-alkyl, (C1-C4)-haloalkyl or (C1-C4)-alkoxy and
    • mB represents 1 or 2,
    • e.g. those in which
    • RB1=cyclopropyl, RB2=hydrogen and (RB3)=2-OMe (“cyprosulfamide”, S4-1),
    • RB1=cyclopropyl, RB2=hydrogen and (RB3)=5-Cl-2-OMe (S4-2),
    • RB1=ethyl, RB2=hydrogen and (RB3)=2-OMe (S4-3),
    • RB1=isopropyl, RB2=hydrogen and (RB3)=5-Cl-2-OMe (S4-4) and
    • RB1=isopropyl, RB2=hydrogen and (RB3)=2-OMe (S4-5);
    • S4c) Compounds from the class of the benzoylsulfamoylphenylureas of the formula (S4c), as described in EP-A-365484,

    • in which
    • RC1, RC2 independently of one another represent hydrogen, (C1-C8)-alkyl, (C3-C8)-cycloalkyl, (C3-C6)-alkenyl, (C3-C6)-alkynyl,
    • RC3 represents halogen, (C1-C4)-alkyl, (C1-C4)-alkoxy, CF3 and
    • mC represents 1 or 2;
    • for example
    • 1-[4-(N-2-methoxybenzoylsulfamoyl)phenyl]-3-methylurea,
    • 1-[4-(N-2-methoxybenzoylsulfamoyl)phenyl]-3,3-dimethylurea,
    • 1-[4-(N-4,5-dimethylbenzoylsulfamoyl)phenyl]-3-methylurea;
    • S4d) Compounds of the N-phenylsulfonylterephthalamide type of the formula (S4d) and salts thereof, which are known, for example, from CN 101838227,

    • in which
    • RD4 represents halogen, (C1-C4)-alkyl, (C1-C4)-alkoxy, CF3;
    • mD represents 1 or 2;
    • RD5 represents hydrogen, (C1-C6)-alkyl, (C3-C6)-cycloalkyl, (C2-C6)-alkenyl, (C2-C6)-alkynyl, (C5-C6)-cycloalkenyl.
    • S5) Active compounds from the class of the hydroxyaromatics and the aromatic-aliphatic carboxylic acid derivatives (S5), for example
    • ethyl 3,4,5-triacetoxybenzoate, 3,5-dimethoxy-4-hydroxybenzoic acid, 3,5-dihydroxybenzoic acid, 4-hydroxysalicylic acid, 4-fluorosalicylic acid, 2-hydroxycinnamic acid, 2,4-dichlorocinnamic acid, as described in WO-A-2004/084631, WO-A-2005/015994, WO-A-2005/016001.
    • S6) Active compounds from the class of the 1,2-dihydroquinoxalin-2-ones (S6), for example
    • 1-methyl-3-(2-thienyl)-1,2-dihydroquinoxalin-2-one, 1-methyl-3-(2-thienyl)-1,2-dihydroquinoxaline-2-thione, 1-(2-aminoethyl)-3-(2-thienyl)-1,2-dihydroquinoxalin-2-one hydrochloride, 1-(2-methylsulfonylaminoethyl)-3-(2-thienyl)-1,2-dihydroquinoxalin-2-one, as described in WO-A-2005/112630.
    • S7) Compounds from the class of the diphenylmethoxyacetic acid derivatives (S7), e.g. methyl diphenylmethoxyacetate (CAS Reg. No. 41858-19-9) (S7-1), ethyl diphenylmethoxyacetate or diphenylmethoxyacetic acid, as described in WO-A-98/38856.
    • S8) Compounds of the formula (S8), as described in WO-A-98/27049,


in which the symbols and indices are defined as follows:

    • RD1 represents halogen, (C1-C4)-alkyl, (C1-C4)-haloalkyl, (C1-C4)-alkoxy, (C1-C4)-haloalkoxy,
    • RD2 represents hydrogen or (C1-C4)-alkyl,
    • RD3 represents hydrogen, (C1-C8)-alkyl, (C2-C4)-alkenyl, (C2-C4)-alkynyl or aryl, where each of the aforementioned carbon-containing radicals is unsubstituted or substituted by one or more, preferably up to three, identical or different radicals from the group consisting of halogen and alkoxy; or salts thereof,
    • nD represents an integer from 0 to 2.
    • S9) Active compounds from the class of the 3-(5-tetrazolylcarbonyl)-2-quinolones (S9), for example
    • 1,2-dihydro-4-hydroxy-1-ethyl-3-(5-tetrazolylcarbonyl)-2-quinolone (CAS Reg. No.: 219479-18-2), 1,2-dihydro-4-hydroxy-1-methyl-3-(5-tetrazolylcarbonyl)-2-quinolone (CAS Reg. No. 95855-00-8), as described in WO-A-1999/000020.
    • S10) Compounds of the formula (S10a) or (S10b)
    • as described in WO-A-2007/023719 and WO-A-2007/023764
      in which

    • RE1 represents halogen, (C1-C4)-alkyl, methoxy, nitro, cyano, CF3, OCF3,
    • YE, ZE independently of one another represent O or S,
    • nE represents an integer from 0 to 4,
    • RE2 represents (C1-C6)-alkyl, (C2-C6)-alkenyl, (C3-C6)-cycloalkyl, aryl; benzyl, halobenzyl,
    • RE3 represents hydrogen or (C1-C6)-alkyl.
    • S11) Active compounds of the oxyimino compounds type (S11), which are known as seed-dressing agents, for example
    • “oxabetrinil” ((Z)-1,3-dioxolan-2-ylmethoxyimino(phenyl)acetonitrile) (S11-1), which is known as a seed-dressing safener for millet/sorghum against metolachlor damage,
    • “fluxofenim” (1-(4-chlorophenyl)-2,2,2-trifluoro-1-ethanone 0-(1,3-dioxolan-2-ylmethyl)oxime) (S11-2), which is known as a seed-dressing safener for millet/sorghum against metolachlor damage, and
    • “cyometrinil” or “CGA-43089” ((Z)-cyanomethoxyimino(phenyl)acetonitrile) (S11-3), which is known as a seed-dressing safener for millet/sorghum against metolachlor damage.
    • S12) Active compounds from the class of the isothiochromanones (S12), for example methyl [(3-oxo-1H-2-benzothiopyran-4(3H)-ylidene)methoxy]acetate (CAS Reg. No. 205121-04-6) (S12-1) and related compounds from WO-A-1998/13361.
    • S13) One or more compounds from group (S13):
    • “naphthalic anhydride” (1,8-naphthalenedicarboxylic anhydride) (S13-1), which is known as a seed-dressing safener for corn against thiocarbamate herbicide damage,
    • “fenclorim” (4,6-dichloro-2-phenylpyrimidine) (S13-2), which is known as a safener for pretilachlor in sown rice,
    • “flurazole” (benzyl 2-chloro-4-trifluoromethyl-1,3-thiazole-5-carboxylate) (S13-3), which is known as a seed-dressing safener for millet/sorghum against alachlor and metolachlor damage,
    • “CL 304415” (CAS Reg. No. 31541-57-8)
    • (4-carboxy-3,4-dihydro-2H-1-benzopyran-4-acetic acid) (S13-4) from American Cyanamid, which is known as a safener for corn against damage by imidazolinones,
    • “MG 191” (CAS Reg. No. 96420-72-3) (2-dichloromethyl-2-methyl-1,3-dioxolane) (S13-5) from Nitrokemia, which is known as a safener for corn,
    • “MG 838” (CAS Reg. No. 133993-74-5)
    • (2-propenyl 1-oxa-4-azaspiro[4.5]decane-4-carbodithioate) (S13-6) from Nitrokemia
    • “disulfoton” (0,0-diethyl S-2-ethylthioethyl phosphorodithioate) (S13-7),
    • “dietholate” (0,0-diethyl 0-phenyl phosphorothioate) (S13-8),
    • “mephenate” (4-chlorophenyl methylcarbamate) (S13-9).
    • S14) Active compounds which, in addition to herbicidal action against harmful plants, also have safener action on crop plants such as rice, for example
    • “dimepiperate” or “MY-93” (S-1-methyl 1-phenylethylpiperidine-1-carbothioate), which is known as a safener for rice against damage by the herbicide molinate,
    • “daimuron” or “SK 23” (1-(1-methyl-1-phenylethyl)-3-p-tolylurea), which is known as a safener for rice against damage by the herbicide imazosulfuron,
    • “cumyluron”=“JC-940” (3-(2-chlorophenylmethyl)-1-(1-methyl-1-phenylethyl)urea, see JP-A-60087270), which is known as a safener for rice against damage by some herbicides,
    • “methoxyphenone” or “NK 049” (3,3′-dimethyl-4-methoxybenzophenone), which is known as a safener for rice against damage by some herbicides,
    • “CSB” (1-bromo-4-(chloromethylsulfonyl)benzene) from Kumiai, (CAS Reg. No. 54091-06-4), which is known as a safener against damage by some herbicides in rice.
    • S15) Compounds of the formula (S15) or tautomers thereof

    • as described in WO-A-2008/131861 and WO-A-2008/131860
    • in which
    • RH1 represents a (C1-C6)-haloalkyl radical and
    • RH2 represents hydrogen or halogen and
    • RH3, RH4 independently of one another represent hydrogen, (C1-C16)-alkyl, (C2-C16)-alkenyl or (C2-C16)-alkynyl,
    • where each of the 3 latter radicals is unsubstituted or substituted by one or more radicals from the group of halogen, hydroxyl, cyano, (C1-C4)-alkoxy, (C1-C4)-haloalkoxy, (C1-C4)-alkylthio, (C1-C4)-alkylamino, di[(C1-C4)-alkyl]amino, [(C1-C4)-alkoxy]carbonyl, [(C1-C4)-haloalkoxy]carbonyl, (C3-C6)-cycloalkyl which is unsubstituted or substituted, phenyl which is unsubstituted or substituted, and heterocyclyl which is unsubstituted or substituted,
    • or (C3-C6)-cycloalkyl, (C4-C6)-cycloalkenyl, (C3-C6)-cycloalkyl fused on one side of the ring to a 4 to 6-membered saturated or unsaturated carbocyclic ring, or (C4-C6)-cycloalkenyl fused on one side of the ring to a 4 to 6-membered saturated or unsaturated carbocyclic ring,
    • where each of the 4 latter radicals is unsubstituted or substituted by one or more radicals from the group of halogen, hydroxyl, cyano, (C1-C4)-alkyl, (C1-C4)-haloalkyl, (C1-C4)-alkoxy, (C1-C4)-haloalkoxy, (C1-C4)-alkylthio, (C1-C4)-alkylamino, di[(C1-C4)-alkyl]amino, [(C1-C4)-alkoxy]carbonyl, [(C1-C4)-haloalkoxy]carbonyl, (C3-C6)-cycloalkyl which is unsubstituted or substituted, phenyl which is unsubstituted or substituted, and heterocyclyl which is unsubstituted or substituted,
    • or
    • RH3 represents (C1-C4)-alkoxy, (C2-C4)-alkenyloxy, (C2-C6)-alkynyloxy or (C2-C4)-haloalkoxy and
    • RH4 represents hydrogen or (C1-C4)-alkyl or
    • RH3 and RH4 together with the directly attached nitrogen atom represent a four- to eight-membered heterocyclic ring which, as well as the nitrogen atom, may also contain further ring heteroatoms, preferably up to two further ring heteroatoms from the group of N, O and S, and which is unsubstituted or substituted by one or more radicals from the group of halogen, cyano, nitro, (C1-C4)-alkyl, (C1-C4)-haloalkyl, (C1-C4)-alkoxy, (C1-C4)-haloalkoxy and (C1-C4)-alkylthio.
    • S16) Active compounds which are used primarily as herbicides but also have safener action on crop plants, for example
    • (2,4-dichlorophenoxy)acetic acid (2,4-D),
    • (4-chlorophenoxy)acetic acid,
    • (R,S)-2-(4-chloro-o-tolyloxy)propionic acid (mecoprop),
    • 4-(2,4-dichlorophenoxy)butyric acid (2,4-DB),
    • (4-chloro-o-tolyloxy)acetic acid (MCPA),
    • 4-(4-chloro-o-tolyloxy)butyric acid,
    • 4-(4-chlorophenoxy)butyric acid,
    • 3,6-dichloro-2-methoxybenzoic acid (dicamba),
    • 1-(ethoxycarbonyl)ethyl 3,6-dichloro-2-methoxybenzoate (lactidichlor-ethyl).

Preferred safeners in combination with the compounds of the general formula (I) according to the invention and/or salts thereof, in particular with the compounds of the formulae (I-1) to (I-662) and/or salts thereof, are: cloquintocet-mexyl, cyprosulfamide, fenchlorazole ethyl ester, isoxadifen-ethyl, mefenpyr-diethyl, fenclorim, cumyluron, S4-1 and S4-5, and particularly preferred safeners are: cloquintocet-mexyl, cyprosulfamide, isoxadifen-ethyl and mefenpyr-diethyl.

Biological Examples

A. Early Post-Emergence Herbicidal Action

Seeds of monocotyledonous or dicotyledonous weed plants were placed in 96-well microtiter plates in quartz sand and grown in a climatized chamber under controlled growth conditions. 5 to 7 days after sowing, the test plants were treated at the cotyledon stage. The compounds according to the invention, formulated in the form of emulsion concentrates (EC), were applied with a water application rate of the equivalent of 2200 liters per hectare. After the test plants had been left to stand in the climatized chamber for 9 to 12 days under optimum growth conditions, the effect of the preparations was scored visually in comparison to untreated controls. For example, 100% activity=the plants have died, 0% activity=like control plants.

Tables A1 to A2 below show the effects of selected compounds of the general formula (I) according to Table 1 on various harmful plants and an application rate corresponding to 1,900 g/ha, which were obtained by the experimental procedure mentioned above.

TABLE A1 Early post-emergence action against Agrostis tenuis (AGSTE) Example Dosage number [g/ha] AGSTE I-591 1900 100 I-595 1900 100 I-649 1900 100

TABLE A2 Early post-emergence action against Poa annua (POAAN) Example Dosage number [g/ha] POAAN I-591 1900 100 I-595 1900 100 I-649 1900 100

The test results show that compounds of the general formula (I) according to the invention, in the case of early post-emergence treatment, have good herbicidal activity against selected harmful plants such as Agrostis tenuis (AGSTE) and Poa annua (POAAN) at a respective application rate of 1900 g of active substance per hectare.

B. Post-Emergence Herbicidal Action and Crop Plant Compatibility

Seeds of mono- and dicotyledonous weed plants were placed in plastic pots in sandy loam soil (doubly sown with in each case one species of mono- or dicotyledonous weed plants per pot), covered with soil and cultivated in a greenhouse under controlled growth conditions. 2 to 3 weeks after sowing, the test plants were treated at the one-leaf stage. The compounds of the invention, formulated in the form of wettable powders (WP) or as emulsion concentrates (EC), were applied onto the green parts of the plants as aqueous suspension or emulsion with addition of 0.5% additive at a water application rate of 600 liters per hectare (converted). After the test plants had been kept in the greenhouse under optimum growth conditions for about 3 weeks, the activity of the preparations was rated visually in comparison to untreated controls. For example, 100% activity=the plants have died, 0% activity=like control plants.

Tables B1 to B8 below show the effects of selected compounds of the general formula (I) according to Table 1 on various harmful plants and an application rate corresponding to 1280 g/ha, which were obtained by the experimental procedure mentioned above.

TABLE B1 Post-emergence action against Echinochloa crus-galli (ECHCG) Example Dosage number [g/ha] ECHCG I-158 1280 100 I-210 1280 90 I-212 1280 100 I-216 1280 100 I-478 1280 90 I-479 1280 100 I-481 1280 100 I-484 1280 100 I-487 1280 100 I-500 1280 90 I-504 1280 90 I-515 1280 100

TABLE B2 Post-emergence action against Poa annua (POAAN) Example Dosage number [g/ha] POAAN I-210 1280 100 I-212 1280 100 I-216 1280 100 I-397 1280 100 I-406 1280 90 I-430 1280 90 I-433 1280 100 I-444 1280 100 I-478 1280 100 I-479 1280 100 I-481 1280 100 I-482 1280 100 I-483 1280 90 I-484 1280 100 I-485 1280 90 I-486 1280 100 I-487 1280 100 I-488 1280 90 I-500 1280 100 I-504 1280 100 I-511 1280 100 I-515 1280 100 I-522 1280 90 I-526 1280 100 I-533 1280 100

TABLE B3 Post-emergence action against Abutilon theophrasti (ABUTH) Example Dosage number [g/ha] ABUTH I-156 1280 100 I-210 1280 90 I-216 1280 100 I-397 1280 90 I-433 1280 90 I-478 1280 100 I-479 1280 100 I-481 1280 100 I-482 1280 90 I-483 1280 90 I-484 1280 100 I-485 1280 90 I-486 1280 90 I-487 1280 100 I-488 1280 100 I-500 1280 100 I-511 1280 90 I-520 1280 90

TABLE B4 Post-emergence action against Amaranthus retroflexus (AMARE) Example Dosage number [g/ha] AMARE I-154 1280 100 I-156 1280 100 I-158 1280 100 I-216 1280 100 I-406 1280 90 I-430 1280 90 I-433 1280 90 I-438 1280 90 I-441 1280 100 I-450 1280 90 I-465 1280 90 I-478 1280 100 I-479 1280 100 I-481 1280 100 I-482 1280 100 I-483 1280 90 I-484 1280 100 I-485 1280 100 I-486 1280 90 I-487 1280 100 I-488 1280 100 I-504 1280 100 I-509 1280 100 I-511 1280 100 I-515 1280 100 I-520 1280 100 I-522 1280 100

TABLE B5 Post-emergence action against Stellaria media (STEME) Example Dosage number [g/ha] STEME I-156 1280 100 I-158 1280 100 I-212 1280 100 I-216 1280 100 I-397 1280 100 I-406 1280 90 I-430 1280 100 I-433 1280 100 I-438 1280 90 I-439 1280 90 I-441 1280 100 I-444 1280 90 I-478 1280 100 I-479 1280 100 I-481 1280 100 I-482 1280 100 I-483 1280 100 I-484 1280 100 I-485 1280 100 I-486 1280 100 I-487 1280 100 I-488 1280 100 I-500 1280 100 I-504 1280 100 I-511 1280 100 I-515 1280 100 I-522 1280 100

TABLE B6 Post-emergence action against Lolium rigidum (LOLRI) Example Dosage number [g/ha] STEME I-478 1280 100 I-479 1280 100 I-481 1280 100 I-484 1280 100 I-511 1280 90 I-515 1280 100

TABLE B7 Post-emergence action against Setaria viridis (SETVI) Example Dosage number [g/ha] STEME I-433 1280 90 I-478 1280 100 I-479 1280 100 I-481 1280 100 I-482 1280 90 I-484 1280 100 I-486 1280 100 I-487 1280 90 I-488 1280 100 I-504 1280 100 I-511 1280 90 I-515 1280 90

TABLE B8 Post-emergence action against Matricaria inodora (MATIN) Example Dosage number [g/ha] STEME I-444 1280 90 I-478 1280 90 I-479 1280 100 I-481 1280 90 I-484 1280 100 I-487 1280 100

The test results show that compounds of the general formula (I) according to the invention, in the case of post-emergence treatment, have good herbicidal activity against selected harmful plants such as Echinochloa crus-galli (ECHCG), Poa annua (POAAN), Abutilon theophrasti (ABUTH), Amaranthus retroflexus (AMARE), Stellaria media (STEME), Lolium rigidum (LOLRI), Setaria viridis (SETVI) and Matricaria inodora (MATIN) at an application rate of 1280 g of active substance per hectare.

C. Pre-Emergence Herbicidal Action and Crop Plant Compatibility

Seeds of mono- and dicotyledonous weed plants were placed in plastic pots in sandy loam soil (doubly sown with in each case one species of mono- or dicotyledonous weed plants per pot) and covered with soil. The compounds of the invention, formulated in the form of wettable powders (WP) or as emulsion concentrates (EC), were then applied onto the surface of the covering soil as aqueous suspension or emulsion with addition of 0.5% additive at a water application rate of 600 liters per hectare (converted). After the treatment, the pots were placed in a greenhouse and kept under good growth conditions for the test plants. After about 3 weeks, the effect of the preparations was scored visually in comparison with untreated controls as percentages. For example, 100% activity=the plants have died, 0% activity=like control plants.

Tables C1 to C8 below show the effects of selected compounds of the general formula (I) according to Table 1 on various harmful plants and an application rate corresponding to 1280 g/ha, which were obtained by the experimental procedure mentioned above.

TABLE C1 Pre-emergence action against Echinochloa crus-galli (ECHCG) Example Dosage number [g/ha] ECHCG I-210 1280 100 I-212 1280 100 I-216 1280 100 I-397 1280 100 I-430 1280 100 I-433 1280 100 I-439 1280 100 I-441 1280 100 I-450 1280 90 I-478 1280 100 I-479 1280 100 I-481 1280 100 I-482 1280 100 I-483 1280 90 I-484 1280 100 I-485 1280 90 I-486 1280 100 I-487 1280 100 I-488 1280 100 I-500 1280 100 I-511 1280 100 I-515 1280 100 I-522 1280 100 I-526 1280 100 I-531 1280 90 I-533 1280 90

TABLE C2 Pre-emergence action against Lolium rigidum (LOLRI) Example Dosage number [g/ha] LOLRI I-210 1280 100 I-212 1280 100 I-216 1280 90 I-397 1280 100 I-406 1280 90 I-430 1280 90 I-433 1280 90 I-441 1280 90 I-444 1280 90 I-450 1280 90 I-465 1280 90 I-478 1280 100 I-479 1280 100 I-481 1280 100 I-482 1280 100 I-483 1280 90 I-484 1280 100 I-485 1280 90 I-486 1280 90 I-487 1280 100 I-488 1280 100 I-500 1280 100 I-504 1280 90 I-509 1280 90 I-511 1280 90 I-515 1280 90 I-520 1280 100 I-522 1280 90 I-534 1280 100

TABLE C3 Pre-emergence action against Poa annua (POAAN) Example Dosage number [g/ha] POAAN I-154 1280 100 I-156 1280 100 I-158 1280 90 I-210 1280 100 I-212 1280 100 I-216 1280 100 I-397 1280 100 I-400 1280 100 I-406 1280 100 I-430 1280 100 I-433 1280 100 I-439 1280 100 I-441 1280 100 I-444 1280 100 I-449 1280 90 I-450 1280 100 I-465 1280 100 I-478 1280 100 I-479 1280 100 I-481 1280 100 I-482 1280 100 I-483 1280 100 I-484 1280 100 I-485 1280 100 I-486 1280 100 I-487 1280 100 I-488 1280 100 I-500 1280 100 I-504 1280 90 I-509 1280 100 I-511 1280 100 I-515 1280 100 I-520 1280 100 I-522 1280 100 I-526 1280 100 I-531 1280 100 I-533 1280 90

TABLE C4 Pre-emergence action against Setaria viridis (SETVI) Example Dosage number [g/ha] SETVI I-154 1280 100 I-156 1280 90 I-158 1280 90 I-210 1280 100 I-212 1280 100 I-216 1280 100 I-397 1280 100 I-400 1280 100 I-405 1280 100 I-406 1280 100 I-430 1280 100 I-433 1280 100 I-439 1280 100 I-441 1280 100 I-444 1280 100 I-450 1280 100 I-465 1280 90 I-478 1280 100 I-479 1280 100 I-481 1280 100 I-482 1280 100 I-483 1280 100 I-484 1280 100 I-485 1280 100 I-486 1280 100 I-487 1280 100 I-488 1280 100 I-500 1280 100 I-504 1280 100 I-509 1280 90 I-511 1280 100 I-515 1280 100 I-520 1280 90 I-522 1280 100 I-526 1280 100 I-531 1280 100 I-533 1280 90 I-534 1280 90

TABLE C5 Pre-emergence action against Abutilon theophrasti (ABUTH) Example Dosage number [g/ha] ABUTH I-210 1280 100 I-212 1280 100 I-216 1280 100 I-397 1280 100 I-430 1280 100 I-433 1280 100 I-438 1280 90 I-439 1280 100 I-441 1280 100 I-450 1280 100 I-478 1280 100 I-479 1280 100 I-481 1280 100 I-482 1280 100 I-483 1280 100 I-484 1280 100 I-485 1280 100 I-486 1280 100 I-487 1280 100 I-488 1280 100 I-500 1280 100 I-504 1280 90 I-509 1280 100 I-511 1280 100 I-515 1280 100 I-520 1280 90 I-522 1280 100 I-526 1280 100 I-531 1280 100

TABLE C6 Pre-emergence action against Amaranthus retroflexus (AMARE) Example Dosage number [g/ha] AMARE I-154 1280 100 I-156 1280 100 I-158 1280 100 I-210 1280 100 I-212 1280 100 I-216 1280 100 I-397 1280 90 I-400 1280 90 I-405 1280 100 I-406 1280 90 I-430 1280 100 I-433 1280 100 I-439 1280 90 I-441 1280 100 I-444 1280 100 I-450 1280 90 I-465 1280 100 I-478 1280 100 I-479 1280 100 I-481 1280 100 I-482 1280 100 I-483 1280 100 I-484 1280 100 I-485 1280 100 I-486 1280 100 I-487 1280 100 I-488 1280 100 I-500 1280 100 I-504 1280 100 I-509 1280 100 I-511 1280 100 I-515 1280 100 I-520 1280 100 I-522 1280 90 I-526 1280 100 I-531 1280 100 I-534 1280 90

TABLE C7 Pre-emergence action against Matricaria inodora (MATIN) Example Dosage number [g/ha] MATIN I-154 1280 100 I-156 1280 90 I-210 1280 100 I-212 1280 100 I-216 1280 100 I-397 1280 100 I-400 1280 90 I-406 1280 100 I-430 1280 100 I-433 1280 100 I-438 1280 100 I-441 1280 100 I-444 1280 100 I-450 1280 100 I-478 1280 100 I-479 1280 100 I-481 1280 100 I-482 1280 100 I-483 1280 100 I-484 1280 100 I-485 1280 100 I-487 1280 100 I-488 1280 100 I-500 1280 90 I-504 1280 90 I-509 1280 100 I-511 1280 100 I-515 1280 100 I-520 1280 100 I-522 1280 90 I-526 1280 100 I-531 1280 100 I-534 1280 90

TABLE C8 Pre-emergence action against Stellaria media (STEME) Example Dosage number [g/ha] STEME I-154 1280 100 I-156 1280 100 I-158 1280 100 I-210 1280 100 I-212 1280 100 I-216 1280 100 I-397 1280 100 I-400 1280 100 I-405 1280 100 I-406 1280 100 I-430 1280 100 I-433 1280 100 I-438 1280 100 I-439 1280 100 I-441 1280 100 I-444 1280 100 I-449 1280 100 I-450 1280 100 I-465 1280 90 I-478 1280 100 I-479 1280 100 I-481 1280 100 I-482 1280 100 I-483 1280 100 I-484 1280 100 I-485 1280 100 I-486 1280 100 I-487 1280 100 I-488 1280 100 I-500 1280 100 I-504 1280 100 I-509 1280 100 I-511 1280 100 I-515 1280 100 I-520 1280 100 I-522 1280 100 I-526 1280 100 I-531 1280 100 I-533 1280 100 I-534 1280 100

The test results show that compounds of the general formula (I) according to the invention, in the case of pre-emergence treatment, have good herbicidal activity against selected harmful plants such as Echinochloa crus-galli (ECHCG), Lolium rigidum (LOLRI), Setaria viridis (SETVI), Poa annua (POAAN), Abutilon theophrasti (ABUTH), Amaranthus retroflexus (AMARE), Stellaria media (STEME) and Matricaria inodora (MATIN) at an application rate of 1280 g of active substance per hectare.

Claims

1. A substituted 2-heteroaryloxypyridine of formula (I) or a salt thereof

in which
X represents nitrogen, —CF— or —CH—,
A represents oxygen, —S(O)n—, —C(R4)(R5)—, —C(═O)— or —NR6— with n=0, 1 or 2,
R1 represents optionally substituted aryl, heteroaryl, heterocyclyl, (C3-C10)-cycloalkyl or (C3-C10)-cycloalkenyl, where each ring or each ring system is optionally substituted by up to 5 substituents independently selected from the group R7;
R2 independently of the others represents halogen, cyano, nitro, formyl, formamide, (C1-C8)-alkyl, (C1-C8)-haloalkyl, (C2-C8)-alkenyl, (C2-C8)-alkynyl, (C2-C8)-haloalkenyl, (C2-C8)-haloalkynyl, (C1-C4)-alkoxy-(C1-C4)-alkyl, (C1-C4)-haloalkoxy-(C1-C4)-alkyl, (C1-C4)-alkylthio-(C1-C4)-alkyl, (C1-C4)-alkylsulfinyl-(C1-C4)-alkyl, (C1-C4)-alkylsulfonyl-(C1-C4)-alkyl, (C1-C8)-alkylcarbonyl, (C1-C8)-haloalkylcarbonyl, (C3-C8)-cycloalkylcarbonyl, carboxyl, (C1-C8)-alkoxycarbonyl, (C1-C8)-haloalkoxycarbonyl, (C3-C8)-cycloalkoxycarbonyl, carbamoyl, (C2-C8)-alkylaminocarbonyl, (C2-C10)-dialkylaminocarbonyl, (C3-C10)-cycloalkylaminocarbonyl, (C1-C4)-alkoxycarbonyl-(C1-C4)-alkyl, (C1-C4)-haloalkoxycarbonyl-(C1-C4)-alkyl, carboxy-(C1-C4)-alkyl, hydroxy, amino, (C1-C8)-alkoxy, (C1-C8)-haloalkoxy, (C1-C8)-alkylthio, (C1-C8)-haloalkylthio, (C3-C8)-cycloalkylthio, (C1-C8)-alkylsulfinyl, (C1-C8)-haloalkylsulfinyl, (C3-C8)-cycloalkylsulfinyl, (C1-C8)-alkylsulfonyl, (C1-C8)-haloalkylsulfonyl, (C3-C8)-cycloalkylsulfonyl, (C1-C8)-alkylaminosulfonyl, (C2-C8)-dialkylaminosulfonyl or (C3-C8)-trialkylsilyl,
m represents 0, 1, 2 or 3,
R3 represents hydrogen, halogen, cyano, nitro, formyl, (C1-C8)-alkyl, (C1-C8)-haloalkyl, (C2-C8)-alkenyl, (C2-C8)-alkynyl, (C2-C8)-haloalkenyl, (C2-C8)-haloalkynyl, (C1-C4)-alkoxy-(C1-C4)-alkyl, (C1-C4)-haloalkoxy-(C1-C4)-alkyl, (C1-C4)-alkylthio-(C1-C4)-alkyl, (C1-C4)-alkylsulfinyl-(C1-C4)-alkyl, (C1-C4)-alkylsulfonyl-(C1-C4)-alkyl, (C1-C8)-alkylcarbonyl, (C1-C8)-haloalkylcarbonyl, (C3-C8)-cycloalkylcarbonyl, carboxyl, (C1-C8)-alkoxycarbonyl, (C1-C8)-haloalkoxycarbonyl, (C3-C8)-cycloalkoxycarbonyl, (C1-C8)-alkylaminocarbonyl, (C2-C8)-dialkylaminocarbonyl, (C3-C8)-cycloalkylaminocarbonyl, hydroxy, (C1-C8)-alkoxy, (C1-C8)-haloalkoxy, (C1-C8)-alkylthio, (C1-C8)-haloalkylthio, (C3-C8)-cycloalkylthio, (C1-C8)-alkylsulfinyl, (C1-C8)-haloalkylsulfinyl, (C3-C8)-cycloalkylsulfinyl, (C1-C8)-alkylsulfonyl, (C1-C8)-haloalkylsulfonyl, (C3-C8)-cycloalkylsulfonyl, (C1-C8)-alkylaminosulfonyl, (C2-C8)-dialkylaminosulfonyl or (C3-C8)-trialkylsilyl,
R4 and R5 independently of one another represent hydrogen, hydroxy, halogen, (C1-C8)-alkyl, (C1-C8)-haloalkyl, (C2-C8)-alkenyl, (C2-C8)-alkynyl, (C1-C4)-alkoxy-(C1-C4)-alkyl, (C1-C4)-haloalkoxy-(C1-C4)-alkyl, (C1-C4)-alkylthio-(C1-C4)-alkyl, (C1-C4)-alkylsulfinyl-(C1-C4)-alkyl, (C1-C4)-alkylsulfonyl-(C1-C4)-alkyl, (C1-C8)-alkylcarbonyl, (C1-C8)-haloalkylcarbonyl, (C3-C8)-cycloalkylcarbonyl, (C1-C8)-alkoxycarbonyl, (C1-C8)-haloalkoxycarbonyl, (C3-C8)-cycloalkoxycarbonyl, (C1-C8)-alkylaminocarbonyl, (C2-C8)-dialkylaminocarbonyl, (C3-C8)-cycloalkylaminocarbonyl, (C1-C8)-alkoxy, (C1-C8)-alkylthio, (C1-C8)-haloalkylthio, (C3-C8)-cycloalkylthio,
or
R4 and R5 together form a 3- to 6-membered carbocyclic ring or a 3- to 6-membered saturated heterocyclic ring having up to 2 oxygen atoms,
or
R4 and R5 together form a (C1-C3)-alkylidene radical or (C1-C3)-haloalkylidene radical,
R6 represents hydrogen, (C1-C8-alkyl, (C1-C8)-haloalkyl, aryl-(C1-C6)-alkyl, heteroaryl-(C1-C6)-alkyl, (C3-C6)-cycloalkyl, (C3-C6)-cycloalkyl-(C1-C6)-alkyl, (C3-C6)-halocycloalkyl, (C3-C6)-halocycloalkyl-(C1-C4)-alkyl, (C2-C8)-alkenyl, (C2-C8)-alkynyl, (C1-C4)-alkoxy-(C1-C4)-alkyl, (C1-C4)-haloalkoxy-(C1-C4)-alkyl, (C1-C4)-alkylthio-(C1-C4)-alkyl, (C1-C4)-alkylsulfinyl-(C1-C4)-alkyl, (C1-C4)-alkylsulfonyl-(C1-C4)-alkyl, (C1-C8)-alkylcarbonyl, (C1-C8-haloalkylcarbonyl, (C3-C8)-cycloalkylcarbonyl, formyl, (C1-C8-alkoxycarbonyl, (C1-C8)-haloalkoxycarbonyl, (C3-C8)-cycloalkoxycarbonyl, (C1-C8)-alkylaminocarbonyl, (C2-C8)-dialkylaminocarbonyl, (C3-C8)-cycloalkylaminocarbonyl,
and
R7 represents hydrogen, halogen, cyano, nitro, formyl, (C1-C8-alkyl, (C1-C8-haloalkyl, (C2-C8)-alkenyl, (C2-C8)-alkynyl, (C2-C8)-haloalkenyl, (C2-C8)-haloalkynyl, (C1-C4)-alkoxy-(C1-C4)-alkyl, (C1-C4)-haloalkoxy-(C1-C4)-alkyl, (C1-C4)-alkylthio-(C1-C4)-alkyl, (C1-C4)-alkylsulfinyl-(C1-C4)-alkyl, (C1-C4)-alkylsulfonyl-(C1-C4)-alkyl, (C1-C8)-alkylcarbonyl, (C1-C8)-haloalkylcarbonyl, (C3-C8)-cycloalkylcarbonyl, carboxyl, (C1-C8)-alkoxycarbonyl, (C1-C8-haloalkoxycarbonyl, (C3-C8)-cycloalkoxycarbonyl, (C1-C8-alkylaminocarbonyl, (C2-C8)-dialkylaminocarbonyl, (C3-C8)-cycloalkylaminocarbonyl, hydroxy, (C1-C8)-alkoxy, (C1-C8)-haloalkoxy, (C1-C8)-alkylthio, (C1-C8)-haloalkylthio, (C3-C8)-cycloalkylthio, (C1-C8-alkylsulfinyl, (C1-C8)-haloalkylsulfinyl, (C3-C8)-cycloalkylsulfinyl, (C1-C8-alkylsulfonyl, (C1-C8)-haloalkylsulfonyl, (C3-C8)-cycloalkylsulfonyl, (C1-C8-alkylaminosulfonyl, (C2-C8)-dialkylaminosulfonyl or (C3-C8)-trialkylsilyl.

2. The compound of formula (I) as claimed in claim 1 or a salt thereof, in which

X represents nitrogen, —CF— or —CH—,
A represents oxygen, —S(O)n—, —C(R4)(R5)—, —C(═O)— or —NR6— with n=0, 1 or 2,
R1 represents optionally substituted aryl, heteroaryl or heterocyclyl, where each ring or each ring system is optionally substituted by up to 5 substituents independently selected from the group R7,
R2 independently of the others represents halogen, cyano, nitro, formyl, formamid, (C1-C4)-alkyl, (C1-C4)-haloalkyl, (C2-C4)-alkenyl, (C2-C4)-alkynyl, (C2-C4)-haloalkenyl, (C1-C4)-alkoxy-(C1-C4)-alkyl, (C1-C4)-haloalkoxy-(C1-C4)-alkyl, (C1-C4)-alkylcarbonyl, (C1-C4)-haloalkylcarbonyl, carboxyl, (C1-C4)-alkoxycarbonyl, (C1-C4)-haloalkoxycarbonyl, (C3-C6)-cycloalkoxycarbonyl, carbamoyl, (C2-C4)-alkylaminocarbonyl, (C2-C6)-dialkylaminocarbonyl, (C1-C4)-alkoxycarbonyl-(C1-C4)-alkyl, (C1-C4)-haloalkoxycarbonyl-(C1-C4)-alkyl, carboxy-(C1-C4)-alkyl, hydroxy, amino, (C1-C4)-alkoxy, (C1-C4)-haloalkoxy, (C1-C4)-alkylthio, (C1-C4)-alkylsulfinyl, (C1-C4)-alkylsulfonyl, (C1-C4)-alkylaminosulfonyl, (C2-C6)-dialkylaminosulfonyl or (C3-C6)-trialkylsilyl,
m represents 0, 1, 2 or 3,
R3 represents hydrogen, halogen, cyano, nitro, formyl, (C1-C4)-alkyl, (C1-C4)-haloalkyl, (C2-C4)-alkenyl, (C2-C4)-alkynyl, (C2-C4)-haloalkenyl, (C2-C4)-haloalkynyl, (C1-C4)-alkylcarbonyl, (C1-C4)-haloalkylcarbonyl, carboxyl, (C1-C4)-alkoxycarbonyl, (C1-C4)-haloalkoxycarbonyl, (C3-C6)-cycloalkoxycarbonyl, (C1-C4)-alkylaminocarbonyl, (C2-C6)-dialkylaminocarbonyl, hydroxy, (C1-C4)-alkoxy, (C1-C4)-haloalkoxy, (C1-C4)-alkylthio, (C1-C4)-haloalkylthio, (C1-C4)-alkylsulfinyl, (C1-C4)-haloalkylsulfinyl, (C1-C4)-alkylsulfonyl, (C1-C4)-haloalkylsulfonyl, (C1-C4)-alkylaminosulfonyl, (C2-C6)-dialkylaminosulfonyl or (C3-C6)-trialkylsilyl,
R4 and R5 independently of one another represent hydrogen, hydroxy, halogen, (C1-C4)-alkyl, (C1-C4)-haloalkyl, (C2-C4)-alkenyl, (C2-C4)-alkynyl, (C1-C4)-alkoxycarbonyl, (C1-C4)-haloalkoxycarbonyl or (C3-C6)-cycloalkoxycarbonyl,
or
R4 and R5 together form a (C1-C3)-alkylidene radical or (C1-C3)-haloalkylidene radical,
R6 represents hydrogen, (C1-C4)-alkyl, (C1-C4)-haloalkyl, aryl-(C1-C4)-alkyl, heteroaryl-(C1-C4)-alkyl, (C2-C4)-alkenyl, (C2-C4)-alkynyl, (C1-C4)-alkylcarbonyl, formyl or (C1-C4)-alkoxycarbonyl,
and
R7 represents hydrogen, halogen, cyano, nitro, formyl, (C1-C4)-alkyl, (C1-C4)-haloalkyl, (C2-C4)-alkenyl, (C2-C4)-alkynyl, (C2-C4)-haloalkenyl, (C2-C4)-haloalkynyl, (C1-C4)-alkoxy-(C1-C4)-alkyl, (C1-C4)-haloalkoxy-(C1-C4)-alkyl, (C1-C4)-alkylcarbonyl, (C1-C4)-haloalkylcarbonyl, carboxyl, (C1-C4)-alkoxycarbonyl, (C1-C4)-haloalkoxycarbonyl, (C3-C6)-cycloalkoxycarbonyl, (C1-C4)-alkylaminocarbonyl, (C2-C6)-dialkylaminocarbonyl, (C3-C6)-cycloalkylaminocarbonyl, hydroxy, (C1-C4)-alkoxy, (C1-C4)-haloalkoxy, (C1-C4)-alkylthio, (C1-C4)-haloalkylthio, (C1-C4)-alkylsulfinyl, (C1-C4)-haloalkylsulfinyl, (C1-C4)-alkylsulfonyl, (C1-C4)-haloalkylsulfonyl, (C1-C4)-alkylaminosulfonyl, (C2-C6)-dialkylaminosulfonyl or (C3-C6)-trialkylsilyl.

3. The compound of formula (I) as claimed in claim 1 or a salt thereof, in which

X represents —CH—, —CF— or nitrogen,
A represents oxygen, sulfur, —CH2— or —NR6—,
R1 represents optionally substituted phenyl, pyrid-2-yl or pyrimid-2-yl, where each ring is optionally substituted by up to 5 substituents independently of one another selected from the group R7,
R2 independently of the others represents fluorine, chlorine, bromine, cyano, methyl, ethyl, trifluoromethyl, methoxy, methoxycarbonylmethyl, carboxylmethyl,
m represents 0, 1, 2 or 3,
R3 represents hydrogen, fluorine, chlorine, cyano, methyl, trifluoromethyl, methoxy, trifluoromethoxy,
R6 represents hydrogen or methyl,
and
R7 represents hydrogen, fluorine, chlorine, bromine, cyano, methyl, trifluoromethyl, methoxy, trifluoromethoxy.

4. A herbicidal composition comprising a herbicidally active amount of at least one compound of formula (I) or salt as claimed in claim 1.

5. The herbicidal composition as claimed in claim 4 in a mixture with one or more formulation auxiliaries.

6. The herbicidal composition as claimed in claim 4, further comprising at least one pesticidally active substance selected from the group consisting of insecticides, acaricides, herbicides, fungicides, safeners, and growth regulators.

7. The herbicidal composition as claimed in claim 6, comprises a safener.

8. The herbicidal composition as claimed in claim 7, comprising cyprosulfamide, cloquintocet-mexyl, mefenpyr-diethyl or isoxadifen-ethyl.

9. The herbicidal composition as claimed in claim 4, further comprising an additional herbicide.

10. A method of controlling one or more unwanted plants, comprising applying an effective amount of at least one compound of formula (I) or salt as claimed in claim 1 or a herbicidal composition thereof to the plants and/or to a site of unwanted vegetation.

11. A product comprising one or more compounds of formula (I) or salt as claimed in claim 1 or herbicidal composition thereof for controlling one or more unwanted plants.

12. The product as claimed in claim 11, wherein the one or more compounds of formula (I) or salts are used for controlling one or more unwanted plants in one or more crops of one or more useful plants.

13. The product as claimed in claim 12, wherein the useful plants are transgenic useful plants.

Referenced Cited
Foreign Patent Documents
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Other references
  • International Search Report for Application No. PCT/EP2019/066197 dated Jul. 29, 2019.
Patent History
Patent number: 11834434
Type: Grant
Filed: Jun 19, 2019
Date of Patent: Dec 5, 2023
Patent Publication Number: 20210276974
Assignee: Bayer Aktiengesellschaft (Leverkusen)
Inventors: Michael Charles McLeod (Frankfurt), Ralf Braun (Ramberg), Anu Bheemaiah Machettira (Frankfurt am Main), Dirk Schmutzler (Hattersheim), Elisabeth Asmus (Hoesbach), Christopher Hugh Rosinger (Hofheim), Elmar Gatzweiler (Bad Nauheim)
Primary Examiner: Kyle A Purdy
Application Number: 17/255,770
Classifications
International Classification: A01N 43/54 (20060101); C07D 401/12 (20060101); A01N 43/40 (20060101);